text:
Why Do Moments of Mindlessness Occur?
I noticed that at key moments, such as when I am using social media in a passive way, or when I am between tasks in daily life, I tend to enter a kind of 'habitual' mode of being. On social media I click aimlessly around, almost compulsively. In my house, I just walk around without much planning or purpose.
What could cause such mindless behaviour?
I am also wondering whether merely paying close attention to lapses in attentiveness and to distracted moments can ultimately lead to the elimination of such habitual behaviours.

If ever have been mindful, such would be actually no question. As to the question how to reach such areas: Dana, Sila, Dana, Sila and Dana Sila, and from time to time, talk on Dhamma, reflecting it.

The hindrances are causes of not being mindful: eg. interest in the world.

In short, the five hindrances disrupt mindfulness.
https://en.m.wikipedia.org/wiki/Five_hindrances
Also related to the five hindrances are the general defilements (kilesas), which also hinders mindfulness.

I am also wondering whether merely paying close attention to lapses in attentiveness and to distracted moments can ultimately lead to the elimination of such habitual behaviours.

It’s a good start. However, one needs to purposely commit to the entire eightfold noble path in order to completely eliminate those behaviors.

In the following talk, it is described that the five hindrances, namely, sensual desire, ill will, sloth and torpor, restlessness and remorse, and doubt, do not just affect a person in meditation. It also affects a person at other times. The five hindrances obsess the mind and enslave the mind. They also appear habitually.
The speaker says that people who commit acts of crime like raping their own daughter, are strongly deluded and enslaved by the hindrances.
Only after attaining and mastering the first jhana, do the five hindrances reduce to a very low level that is not significant enough to be considered hindrances any more. After attaining the fourth jhana, the five hindrances are nearly completely eliminated.
The speaker says that a person who has overcome the five hindrances is capable of yoniso manasikara (focused attention or careful attention). With this, a person could attain stream entry simply by listening to the true Dhamma (teachings) attentively and reflecting on it. This is based on SN 55.5.
So, why do moments of mindlessness occur? It's due to the presence of the five hindrances.
In the YouTube video entitled "Characteristics of a Sotapanna" at timestamp 25:52, Ven. Dhammavuddho Mahathera stated (with some paraphrasing):

The third condition, this word - yoniso manasikara, which I
  translate as focused attention. It is also known as careful attention.
  This word means that when you listen to the Dhamma, you are focused on
  listening to the Dhamma. In other words, at that time, you don't have
  the five hindrances. If that is so, then you can understand the Dhamma
  and attain stream entry.
So who are the people who do not have the five hindrances? In the
  suttas, it is stated by the Buddha that as long as a person has not
  attained piti and sukha which are secluded from unwholesome
  states, which are secluded from sensual pleasures, the five hindrances
  will obsess him and obsess him habitually.
So, there are two types of persons who do not have the five
  hindrances. The first is the one who has attained the first jhana
  (i.e. he who has attained piti and sukha). When a person has attained
  the first jhana, he has eliminated the five hindrances and the Buddha
  says that the five hindrances no longer obsess that person habitually.
  ...
So there are two conditions if a person has the hindrances. Firstly,
  it obsesses your mind, it enslaves your mind. Secondly, it is
  habitual, it is very often there. That's why when
  somebody rapes his daughter or rapes his granddaughter,
  it's because he cannot control these hindrances. His
  hindrances overwhelms his mind, obsesses the mind. After a person
  attains the first jhana, the Buddha says that the five hindrances are
  eliminated.
A lot of people don't believe it because they don't really understand
  the hindrances. If I ask you what are the hindrances, a lot of people
  will say sensual desire, ill will, sloth and torpor, restlessness and
  worry, and doubt. But these are not the five hindrances. These are
  called the five hindrances only when they obsess your mind, when they
  enslave your mind and they recur habitually. Only then they are called
  the five hindrances.
When a person attains the first jhana, these five hindrances reduce to
  a low level. They are still there but they are not called hindrances
  any more. It's just as if you walk through a jungle, you may
  encounter seven foot high long grass obstructing you. It's a
  hindrance because when you try to go through it, you cannot see in
  front of you. Secondly, it cuts or injures your skin. So, it's a big
  hindrance. But if I cut down that long grass to 12 inches, it is no
  more a hindrance. But it is still observable.
So, when a person attains  the first jhana,
  it's as if the seven foot high long grass has
  been cut down to 12 inches. When he attains the second jhana,
  the 12 inches becomes 8 inches.
  When he attains the third jhana, it becomes 4
  inches. When he attains the fourth jhana, it becomes one millimeter.
  So there is a big difference between the first three jhanas and the
  fourth jhana.
That is why it is said that once a person attains the first jhana, the
  hindrances are (nearly) eliminated,
  meaning generally (nearly) eliminated for good.

You're off to a good start, in that you are aware of periods when mindfulness is absent. When does this awareness occur? Much later, just after, or during? Try to catch it sooner. Be like a detective, and trace mindlessness back to it's source. See if you can remember what conditioned it. The sooner you catch it, the easier the trace will be.
Everything is conditioned. If we can observe mindlessness non-judgmentaly (or anything else) as they arise, the conditions that give rise will become known. Know what gives rise to it's coming, and what gives rise to it's disappearance. Know what it is like during mindfulness, and what it is like without. Observe keenly, as though you were expected to report on it later. Develop a keen interest in what's actually happening, and experience it fully for yourself.
It is not enough to simply hold the object with your attention, one must "rub" into the object, so to speak, to understand it moment to moment. Observe how it changes and disappears. The conditions that give rise to mindlessness will become obvious. Often, it is the hindrances - clinging, aversion, sloth, restlessness, and doubt. The hindrances are simply the mind out of balance. Rebalance yourself in the middle way and mindfulness will become more effortless.
For example, becoming mindless while browsing the internet is probably both sloth, aversion, and craving - to lazy to do something else, desiring a good story to make you laugh, aversion towards being bored, etc.


text:
Sloth and the Hindrances
In ven. Nyanaponika Thera's compilation, The Five Mental Hindrances and Their Conquest, some aspects seem to recur:

One should attend to hindrances -- sloth included -- with wise attention and not unwise attention. What is meant by this?
For sloth, one should contemplate the drawbacks of sloth (e.g. meditate on death, on suffering) and on inspiring topics (e.g. sympathetic joy, spiritual journey, master's greatness). Are inspiring topics of contemplation natural remedies against sloth? If so, would being moved and experiencing awe counter sloth as well?

Such states as awe or being moved have been studied and valued in psychology, but I have never seen them opposed to laziness or lack of motivation. It just seems to me that the topics of contemplation mentioned in the Five Hindrances text most likely elicit elevation and a sense of meaning in their practitioner.

Yoniso manasikāra as such means “directing the attention to the roots of things,” that is, observing
  phenomena as they truly are, as being characterized by impermanence, unsatisfactoriness and not-self.

Yoniso Manasikāra Sampadā Sutta
You should know the experience of the hindrances are also impermanence, unsatisfactoriness and not-self.

If so, would being moved and experiencing awe counter sloth as well?

Stimulating the mind may result in sloth on the downturn when stimulation is ending.

Great question! There are multiple approaches to counter sloth, as indicated in the article. Sloth and torpor are essentially an imbalance of energy, being on the lower end of the energy spectrum. The ideas for counters are naturally those things that arose energy of the sort that will refresh and buoy the mind. The goal isn't to swing as a pendulum from one extreme to the other, but to slowly bring it to the center - perfectly balanced between relaxation and excitement.
Wise attention is keeping something's origin in mind, seeing to know the causal relationships, and to pay attention to arising phenomena in such a way as to understand clearly their true nature - impermanent, unsatisfying, and Not-Self. Wise attention is the dawn, the forerunner of the Noble Eightfold Path. So, watch the hindrances thusly - observe so as to know their conditioned origin, know how they arise and fall, know that they are impermanent, not you, and are indeed unsatisfying.
Inspiring topics can counter sloth, but the topic should be one that directs you toward balance, toward the Dhamma, toward peace and relinquishment. Battle speeches may be inspiring, but may also over agitate the mind and inspire wandering thoughts. I find good Dhamma talks or books can be very inspiring in the right doses, and invigorate a slothful mind. On long retreats, one may get quite exhausted at times - but a good Dhamma talk can be like the strong arm of a good friend pulling you back up to your feet.
Experiences of awe, being moved, wonder, etc. also can work, if treated with wise attention and bring one to balance. They can be over-stimulating and lead to restlessness as well. For example, if you have an amazing meditative experience, have some nimitta or bright lights of joy or Piti, one may feel awe, moved to tears, and then firmly attach, cling, and identify with these experiences. But with wise attention, we are not trapped by such, and let those go too. They can be motivating - if it gets us on the cushion for the right reason, great. It shouldn't be to replicate those feelings or recreate experience or attain something specific though.

Ajahn Brahm wrote the following in his essay entitled "Five Hindrances".
Wise attention here refers to: "A skillful meditator keeps a sharp look-out for the first signs of sloth and torpor and is thus able to spot its approach and take evasive action before it's too late".
The method to overcome sloth and torpor is written in the quote below i.e. by rousing energy through developing interest.

Sloth and torpor refers to that heaviness of body and dullness of mind
  which drag one down into disabling inertia and thick depression. The
  Lord Buddha compared it to being imprisoned in a cramped, dark cell,
  unable to move freely in the bright sunshine outside. In meditation,
  it causes weak and intermittent mindfulness which can even lead to
  falling asleep in meditation without even realising it!
Sloth and torpor is overcome by rousing energy. Energy is always
  available but few know how to turn on the switch, as it were. Setting
  a goal, a reasonable goal, is a wise and effective way to generate
  energy, as is deliberately developing interest in the task at hand. A
  young child has a natural interest, and consequent energy, because its
  world is so new. Thus, if one can learn to look at one's life, or
  one's meditation, with a 'beginner's mind' one can see ever new angles
  and fresh possibilities which keep one distant from sloth and torpor,
  alive and energetic. Similarly, one can develop delight in whatever
  one is doing by training one's perception to see the beautiful in the
  ordinary, thereby generating the interest which avoids the half-death
  that is sloth and torpor.
The mind has two main functions, 'doing' and 'knowing'. The way of
  meditation is to calm the 'doing' to complete tranquillity while
  maintaining the 'knowing'. Sloth and torpor occur when one carelessly
  calms both the 'doing' and the 'knowing', unable to distinguish
  between them.
Sloth and torpor is a common problem which can creep up and smother
  one slowly. A skillful meditator keeps a sharp look-out for the first
  signs of sloth and torpor and is thus able to spot its approach and
  take evasive action before it's too late. Like coming to a fork in a
  road, one can take that mental path leading away from sloth and
  torpor. Sloth and torpor is an unpleasant state of body and mind, too
  stiff to leap into the bliss of Jhana and too blinded to spot any
  insights. In short, it is a complete waste of precious time.

The advice from SN 9.2 (below) would also be helpful:

Now at that time that mendicant fell asleep during the day’s
  meditation. The deity haunting that forest had compassion for that
  mendicant, and wanted what’s best for them. So they approached that
  mendicant wanting to stir them up, and addressed them in verse:

“Get up, mendicant! Why lie down?
    What’s the point in your sleeping?
    What slumber can there be for those afflicted,
    injured, pierced by an arrow?
You should amplify the faith
    that led you to go forth
    from the home life to homelessness.
    Don’t fall under the sway of slumber.”

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text:
Attending Mindfully Versus Without Mindfulness
In this answer by ven. Yuttadhammo, it is said that depending on the level of concentration and mindfulness of a person, attending to certain states can result in either wakefulness or tiredness. Hence, I wonder:
Is it the case that strong mindfulness tends to counter unwholesome states merely by observation, and that without mindfulness these states persevere and may worsen? E.g. a person meditating on a bus mindfully will decrease hindrances, whereas a person mindwandering might increase them?
If so, then I ask:
Does this entail that strong meditative states 'burn' unwholesome states because of a mindfulness absent from daily life?

Ayoniso manasikāra, as such, means “not directing the attention to the roots of things” or “directing
the attention away from the roots of things,” that is, not observing phenomena as they truly are, not noticing that they are impermanent, unsatisfactory and not-self

Yoniso Manasikāra Sampadā Sutta

Yoniso manasikāra as such means “directing the attention to the roots of things,” that is, observing
phenomena as they truly are, as being characterized by impermanence, unsatisfactoriness and not-self.

Yoniso Manasikāra Sampadā Sutta

OP: without mindfulness these states persevere and may worsen?
... As a result, wrong view arises, and when this
become a habit, wrong view is reinforced so that it remains as a latent tendency (anusaya)

Yoniso Manasikāra Sampadā Sutta

OP: a person meditating on a bus mindfully will decrease hindrances, whereas a person mindwandering might increase them?

If you have initial and sustained application this will reduce hindrances. Mindfulness accompanies by initial and sustained application will decrease it.

With mindfulness there is acknowledgment of the thoughts and hindrances so they don't get energy.And when there is application of mindfulness on all thoughts and hindrances ,even with the feeling of a self that has to do something .When you uproot that from your consciousness you are truly free,for you there is just phenomenon ,life is luminous beautiful play ,and you simply let it happen including yourself.You let the hindrance come and go you let sadness and happiness come and go ,everything.

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text:
Right time, Right time! But what is the right time to speak?
Failue, disappeared, they say: "Right time, right time. It wasn't the proper time!", but:
What's the right time to ask?
What's the right time to advise?
What's the right time to speak?
What's the right time to stay silent?
What's the right time for delay?
May one answer when ever thought being the right time.
[Not given for trade, exchange, stacks or whatever binds to this wheel but for gaining release from it.]

For context this question might be asking about the phrase, "the Tathagata knows the time to use such speech", in MN28 (quoted in this answer in reply to the question, Don't teach Dhamma to those who can't appreciate it or aren't interested).

The question is tagged abhidhamma -- are you only looking for answers which are based on the Abhidhamma (and not e.g. the Suttas or the Vinaya)?

There is no real Sila without Abhidhamma, Nyom Chris.

In the sutta (MN 28), the phrase "right time" is in the translation of kālaññū which is defined in dictionaries here ("one who knows the proper time"), and here.

Kālaññū knowing the proper time for ... (c. Dat. or Loc.) Sn. 325; described at A. IV, 113 sq.; as one of the five qualities of a rājā cakkavattī (viz. atthaññū, dhamma°, matta°, k°, parisa°) A. III, 148; one of the seven qual. of a sappurisa, a good man (=prec. +atta°, puggala°) D. III, 252, 283; as quality of the Tathāgata D. III, 134=Nd2 276; Pug. 50.

The most complete explanation of kālaññū that I found in the suttas is in Dhammaññūsutta (AN 7.68).
The definition in that context is:

And how are they one who knows the right time? It’s when a mendicant knows the right time: ‘This is the time for recitation; this is the time for questioning; this is the time for meditation; this is the time for retreat.’

In that sutta it's one of seven qualities:

A mendicant with seven qualities is worthy of offerings dedicated to the gods, worthy of hospitality, worthy of a religious donation, worthy of veneration with joined palms, and is the supreme field of merit for the world. What seven? It’s when a mendicant knows the teachings, knows the meaning, has self-knowledge, knows moderation, knows the right time, knows assemblies, and knows people high and low.

Of these seven, the quality with the longest description is the last (I abbreviate slightly in the quote below):

And how are they one who knows people high and low? It’s when a mendicant understands people in terms of pairs. Two people:

one likes to see the noble ones, one does not.
one likes to hear the true teaching, one does not
one lends an ear to the teaching, one does not
one remembers the teaching they’ve heard, one does not
one reflects on the meaning of the teachings they have remembered, one does not
one understands the meaning and the teaching and practices accordingly, one understands the meaning and the teaching but does not practice accordingly
one practices to benefit themselves but not others, and one practices to benefit both themselves and others

That’s how a mendicant understands people in terms of pairs.

The definition of "one who knows assemblies" might be relevant too:

And how are they one who knows assemblies? It’s when a mendicant knows assemblies: ‘This is an assembly of aristocrats, of brahmins, of householders, or of ascetics. This one should be approached in this way. This is how to stand, to act, to sit, to speak, or to stay silent when there.’ If a mendicant did not know assemblies, they would not be called ‘one who knows assemblies’. But because they do know assemblies, they are called ‘one who knows assemblies’. Such is the one who knows the teachings, the one who knows the meaning, the one who has self-knowledge, the one who knows moderation, the one who knows the right time, and the one who knows assemblies.

There's a discussion on SuttaCentral at the moment, ‘Qualifications’ neccesary to teach Dhamma? There someone said that the situation e.g. relationship with a teacher is different within the Sangha: I recommend this answer (which I won't quote here) and the answer immediately following that.

There is no real explaining on what is the right time, Nyom. There are of course indications that right time may be different in dependency of outward condition.

It seems to me that the sutta mentions mostly "inward" conditions (e.g. several types of knowledge), as well as "outward" conditions (e.g. the time and the people in the audience). From other suttas a "proper time" also seems to depend on inter-personal relationships, for example "after being asked".

You're right this answer isn't very specific; but the question is very broad. I made the question narrower by relating it to this comment, where the topic seems to be asking what the suttas say about the "right time" for a monk (and/or the Tathagata) to teach dhamma.

"In and of itself", Nyom Chris. 1 Topic/question. And in the right time.

What's the right time to ask?

When one feels the person is willing to give.

What's the right time to advise?

When one feels the person is willing to take the advice.

What's the right time to speak?

When one feels the person is willing to listen and what one says will have the best impact.

What's the right time to stay silent?

When one feels the person is not willing to listen or will take it the wrong way or what one says will not have and impact.

What's the right time for delay?

When one feels the person is not willing to listen or take advice but this may change for the better. E.g. There are times when the Buddha has delays teaching the Dhamma when one is hungry as one will not be attentive.

Suttas apart, sometimes it's about knowing/understanding the other person.

Mind readers? Or ego-manics? Is there any case that one whould not ask, speak... if he would "feel" it's not of benefit? So what, so how, should feel here be understood, if useful. (don't forget the other 37 who just read and wait on householders answer.

@ Samana Johann feel is only a real time reference of information based on it the action is taken.Its combination of real-time information and memory ,there is no other reference for information on the basis of which to act.


text:
Nature of Direct Experience
I have observed that during contemplation, there are periods where attention is on the object, a kind of basic awareness. Then, there are periods where thoughts emerge, based on the object, a kind of cognition of the object.
Then, there seems to be periods where cognitions unrelated to an object within experience occur; these would be be as mind-wandering or speculation.
My question is: Are those cognitions and fabrications unrelated to direct experience precisely what one tries to counter in Buddhism?
I have the impression that if I cognized only direct experience through awareness, and produced only object-related cognitions, that I would diminish wrongness and inefficiency in the mind greatly.
Thank you

Samsara is mind body industrial music

You might want to study the Structural Defferential. It is a map of the process of abstraction of our nervous system. It was created by Alfred Korzybski, a pioneer in the field of General Semantics.

The basic awareness you're mentioned in your question refers to the silent levels of awareness. This experience of direct awareness of the whole is also called Gestalt.
In Buddha's spiritual path one tries to see and stop the process of "I" making and "mine" making in his mind. That's what I know theoretically.

The work of Korzybski is extremely useful imo as well.

I have a feeling that one can never possibly become a real thinker without understanding the works of Korzybski. And that is only what comes before real monkhood. In other words, one must be an accomplished, expert thinker, before one can become sadhu.

J. Krishnamurti defined the highest level of intelligence as: "The ability to observe without evaluating is the highest form of intelligence." That sound similar to silent levels or direct experience that Korzybski is talking about. Direct experience or just seeing - when you finally see things.

cleaning the mind is not done by focusing on objects of perceptions. This is wrong territory according to the budhha https://suttacentral.net/sn47.7/en/sujato
The right things to watch are whatever is left after the ''five kinds of sensual stimulation'', ie ''cattāro satipaṭṭhānā.''

On the impression; looks close to me. Whether one thinks or not is far less important than the content of thought. That to which one gives frequent attention becomes the inclination, therefore to establish a perception of impermanence ie one has to reflect on impermanence, this is in the Grimananda Sutta; 'how does one develop perception of impermanence? One reflects thus; ..' . Perceptions have to be established by reasoning. Reasoning is like talking to oneself, reasoning one performs actions; be it inference, translation or multiplication; by means of this or that system of expression one communicates internally. Purpose of reasoning is probably the mapping out of what can be thought about as it actually is so that there is no delusion about the cause and effect which results in unforseen consequences and disappontment.


text:
Nature of Craving in Charm and Impressing Others
I noticed recently that I tend to try and impress others and gather attention, especially with women (I'm a man). I see this as problematic because unlike other sources of craving and attachment, its hard to avoid others.
Thus, I'd like to understand the nature of the craving/grasping/etc. process in relation to trying to impress. What type(s) of attachment(s) are involved? How can one best relinquish a need to appear a certain way to others?
Also, I wonder: Is there any equivalent to 'overcompensating' in Buddhism? Overcompensating here means specifically attempting to augment the self because the self is in reality lacking, insecure. How does no-self affect this?
Thank you

What type(s) of attachment(s) are involved?

This is carving arising due to self-view.
There are 18 internal and external views across past, present and future making a total of 108 views of self rooted in carving.
18 Internal Preoccupations with Craving

(1) “I am”
(2) “I am this [I am like this]”
(3) “Thus am I [I am like that]”
(4) “I am otherwise”
(5) “I do not exist”
(6) “I exist”
(7) “May I be”
(8) “May I be this [be like this]”
(9) “May I be so [be like that]”
(10) “May I otherwise”
(11) “I might be”
(12) “I might be this [be like this]”
(13) “I might be that [be like that]”
(14) “I might be otherwise”
(15) “I shall be”
(16) “I shall be this [be like this]”
(17) “I shall be so [be like that]”
(18) “I shall be otherwise”

Tanhā Jālinī Sutta / (Vicarita) Tanha Sutta
18 External Preoccupations with Craving

(1) by this (form, etc), “I am”
(2) by this, “I am this [I am like this]”
(3) by this, “Thus am I [I am like that]”
(4) by this, “I am otherwise”
(5) by this, “I do not exist”
(6) by this, “I exist”
(7) by this, “May I be”
(8) by this, “May I be this [be like this]”
(9) by this, “May I be so [be like that]”
(10) by this, “May I otherwise”
(11) by this, “I might be”
(12) by this, “I might be this [be like this]”
(13) by this, “I might be that”
(14) by this, “I might be otherwise”
(15) by this, “I shall be”
(16) by this, “I shall be this”
(17) by this, “I shall be so”
(18) by this, “I shall be otherwise”

Tanhā Jālinī Sutta / (Vicarita) Tanha Sutta
With regard to external preoccupation with every interaction, one reinforces the self-view with further escalate to sensation resulting in the craving.

"by this experience or interaction, I look good and I appear positively"
"by this experience or interaction, I look good but I appear negatively"
"by this experience or interaction, I look good but I appear neutral"
"by this experience or interaction, I look bad and I appear positively",
"by this experience or interaction, I look bad but I appear negatively"
"by this experience or interaction, I look bad but I appear neutral"
"by this experience or interaction, I look neutral and I appear positively"
"by this experience or interaction, I look neutral but I appear negatively"
"by this experience or interaction, I look neutral but I appear neutral"

More the one appears positive with respect to the self-evaluation and the perception one appear, one experiences deeper shades of pleasantness. Similarly with it is negative one experiences unpleasantness. When there is no disparity, i.e., one's evaluation of oneself matches one's expectation of how one is perceived by others, there is a neutral sensation.
This is further appplified based on the people one tries to project the evaluation, the level one want to make an impression, the number of people involved as well as the source of the experience. The grouping of people could be:

oneself
special people (friends, foes, coworkers and family)
acquainted people
strangers

If the source is a close person then the feeling is more. If a loved one does something unexpected one feels more strongly than a stranger. E.g. if someone you admire is negative about you the pain is more.
If something about you is known by many vs few it will increase the feeling. E.g. if someone does something improper and is caught one may try to stop the knowledge of it spreading as one sees this as damaging.
If one it trying hard to impreses then this also will intensify the sensations. E.g. If one does badly at school it might be harder to let your parents know the results than a stranger who does not care as much.
The combinations give different shares of feelings:

something done by a special person, which affects how I want to project my self, which is projected to other special people
something done by a special person, which does not affects how I want to project my self, which is projected to other special people
something done by a special person, which affects how I want to project my self, which is projected to other people who I care about
something done by a special person, which affects how I want to project my self, which is projected to other people who are strangers

...

How can one best relinquish a need to appear a certain way to others?

This is by eliminating the classes of craving leading to self-view.

You beat me to it, haha... Thanks for a thorough answer.

What type(s) of attachment(s) are involved?
Is there any equivalent to 'overcompensating' in Buddhism?

The attachment/overcompensation you describe can be seen as self-doctrine clinging (attavadupadana).
It is associated with self-view (sakkaya-ditthi), meaning that the five skandhas are mistaken for a self. Self-view runs the risk to cause a struggle for controlling/own/achieve things that are ultimately impermanent, and out of our grasp. Suffering will follow.

How can one best relinquish a need to appear a certain way to others?

Vipassana meditation probably wouldn’t hurt. It can give us a new perspective on the things that are difficult.


text:
Do Different Meditations Support One Another?
I have tried meditating on compassion, just as I've tried meditating on the breath. Currently, these days, I find it hard to meditate on compassion.
My question is: Would practising meditation of any kind improve a meditation of another kind, e.g. practising breath meditation would increase compassion meditation's effectiveness?
Simply put, does every meditation type share at least some aspects with others, some basic features such as--I suppose--gathering attention, learning patience, and so on? Thus, improving those aspects through breath meditation might extend to compassion meditation?
Thank you

Only right view supports meditation for long lasting happiness, liberation, if such is objected. Up on right view one is free to choose the preferred kammatthana according to ones inclinations. To increase right view: practicing dana, sila, bhavana. Once Sila is firm, based on right view, right concentration comes by it's cause given by itself.

Yes they do support eachother imho. Whenever one directs the mind to a wholesome theme, to rouse gladness or energy, when keeping the mind on the theme one is not oblivious to the theme and this concentration is a good skill to develop. Furthermore the foremost quality for the attainment and awakening to the truth is effort and it requires contemplation and coming to agreement.
Therefore it is evident that when mind is somehow impaired one should direct the mind to a skillful theme for a purpose of gladdening or composing otherwise. When mind is unconstricted and pliant one can then retreat from that wholesome theme and stop thinking about it and just be mindful and at ease.
Traditionally speaking the guardian meditations are largely accepted to be necessary among insight and samatha meditators alike afaik. I advocate contemplation in general; https://docs.google.com/document/d/1kZxstsAvjhj9Svc47RUKRIyKQMuHMD4adIvr_7pp2uI/edit?usp=drivesdk

“There is the case of a monk who remains focused on the body in & of itself—ardent, alert, & mindful—subduing greed & distress with reference to the world. As he remains thus focused on the body in & of itself, a fever based on the body arises within his body, or there is sluggishness in his awareness, or his mind becomes scattered externally. He should then direct his mind to any inspiring theme. As his mind is directed to any inspiring theme, delight arises within him. In one who feels delight, rapture arises.
In one whose mind is enraptured, the body grows calm. His body calm, he feels pleasure. As he feels pleasure, his mind grows concentrated.
He reflects, ‘I have attained the aim to which my mind was directed. Let me withdraw [my mind from the inspiring theme].’ He withdraws & engages neither in directed thought nor in evaluation. He
  discerns, ‘I am not thinking or evaluating. I am inwardly mindful & at ease.’
“This, Ananda, is development based on directing.
And what is development based on not directing? A monk, when not directing his mind to external things, discerns, ‘My mind is not directed to external
  things. It is unconstricted [asankhitta] front & back—released & undirected. And then, I remain focused on the body in & of itself. I am ardent, alert, mindful, & at ease.’
“When not directing his mind to external things, he discerns, ‘My mind is not directed to external things. It is unconstricted front & back—released & undirected. And then, I remain focused on feelings… mind… mental qualities in & of themselves. I am ardent, alert, mindful, & at ease.’
“This, Ananda, is development based on not directing.

Metta meditation helps achieve concentration hence will help Anapana

(8) One’s mind easily concentrates.

(Ekā,dasa) Mettânisaṁsā Sutta
Manranasati meditation helps develop a sense of urgency hence you might not be lethargic or procrastinate in meditation.


text:
Sense of Accomplishment in Meditation
Regardless of a meditation's perceived quality, I feel that finishing a meditation provides some sense of accomplishment.
Nowadays, I am experiencing great lack of motivation, and when I set the goal of meditation as '30 minutes', I stop half-way and feel that I failed.
Knowing how finishing things provides accomplishment, would it make more sense setting shorter times which I can finish? Is there such a thing as the momentum of accomplishment in meditation or even in virtuous activity in general? Or, is such a feeling of success a kind of attachment, and problematic?
Thank you

Here are some excellent advice given by Ajaan Fuang in "Awareness Itself":

§ "When the meditation goes well, don't get excited. When it doesn't
  go well, don't get depressed. Simply be observant to see why it's
  good, why it's bad. If you can be observant like this, it won't be
  long before your meditation becomes a skill."
§ A young nurse practiced meditation with Ajaan Fuang several days
  running, and finally asked him one day, "Why wasn't today's session as
  good as yesterday's?"
He answered: "Meditating is like wearing clothes. Today you wear
  white, tomorrow red, yellow, blue, whatever. You have to keep
  changing. You can't wear the same set of clothes all the time. So
  whatever color you're wearing, just be aware of it. Don't get
  depressed or excited about it."
§ A few months later the same nurse was sitting in meditation when a
  sense of peace and clarity in her mind became so intense that she felt
  she would never have a bad mood infiltrate her mind again. But sure
  enough, bad moods eventually came back as before. When she mentioned
  this to Ajaan Fuang, he said, "Looking after the mind is like raising
  a child. There will have to be bad days along with the good. If you
  want only the good, you're in for trouble. So you have to play
  neutral: Don't fall in with the good or the bad."
§ A student came to complain to Ajaan Fuang that she had been
  meditating for years, and still hadn't gotten anything out of it. His
  immediate response: "You don't meditate to 'get' anything. You
  meditate to let go."
§ "Don't make a journal of your meditation experiences. If you do,
  you'll start meditating in order to have this or that thing happen, so
  that you can write it down in your journal. And as a result, you'll
  end up with nothing but the things you've fabricated."
§ "You can't plan the way your practice is going to go. The mind has
  its own steps and stages, and you have to let the practice follow in
  line with them. That's the only way you'll get genuine results.
  Otherwise you'll turn into a half-baked arahant."
§ "When the mind's not quiet — that's when its poor and burdened with
  difficulties. It takes molehills and turns them into mountains. But
  when the mind is quiet, there's no suffering, because there's nothing
  at all. No mountains at all. When there's a lot to the mind, it's
  simply a lot of defilement, making it suffer."

Maybe you can give yourself the flexibility of meditating between 15 to 30 minutes. At the end of it, don't cling to any result/ state, and be observant about why today's session was the way it was. If today's session was not good, it's not because you had failed. It was probably due to some defilement entering the mind. Then that would lead you to identify how the defilement came into the mind. That's more skillful than blaming yourself.

So then I should keep the 30 min, but not cling to any result/state?

Maybe you can give yourself the flexibility of meditating between 15 to 30 minutes. At the end of it, don't cling to any result/ state, and be observant about why today's session was the way it was. If today's session was not good, it's not because you had failed. It was probably due to some defilement entering the mind. Then that would lead you to identify how the defilement came into the mind. That's more skillful than blaming yourself.

when I sit meditation, I sit till I get up. Sometimes that's 15m. Sometimes that's 90m. When I walk meditation, I walk the same path till I get home. The time varies. There's no magic in 30.

Yes, you can develop a momentum in meditation. After consistent and prolonged practice with discipline, meditation get's it's momentum. I know this from mantra meditation. You fill your mind with spiritual impressions. In beginning it won't be easy because your miind is not used to meditation. But over time, as you get used to the practice of meditation, it will be easier and easier to start meditating.

Knowing how finishing things provides accomplishment, would it make more sense setting shorter times which I can finish?

That seems like a situation where you would oblige your craving.

Is there such a thing as the momentum of accomplishment in meditation or even in virtuous activity in general?

Yes. But momentum in a buddhist sense is likely to occur by letting go of attachment or achieving. It’s the art of no art to paraphrase Bruce Lee.

Or, is such a feeling of success a kind of attachment, and problematic?

Yes and yes.

If you struggle with motivation you can consider formally contemplating, can even start with 3-5 minutes.
Mn95;

"Exertion is most helpful for the final attainment of the truth, Bharadvaja. If one didn't make an exertion, one wouldn't finally attain the truth. Because one makes an exertion, one finally attains the truth. Therefore, exertion is most helpful for the final attainment of the truth."
"But what quality is most helpful for exertion? We ask Master Gotama about the quality most helpful for exertion."
"Contemplating is most helpful for exertion, Bharadvaja. If one didn't contemplate, one wouldn't make an exertion. Because one contemplates, one makes an exertion. Therefore, contemplating is most helpful for exertion."
"But what quality is most helpful for contemplating?..."
"Being willing... If one weren't willing, one wouldn't contemplate..."
"But what quality is most helpful for being willing?..."
"Desire... If desire didn't arise, one wouldn't be willing..."
"But what quality is most helpful for desire?..."
"Coming to an agreement through pondering dhammas... If one didn't come to an agreement through pondering dhammas, desire wouldn't arise..."

I would also beware of this line of thinking; 'I am good/bad because of "X". It affirms and is of the notion of 'I am' which is a verbalization of craving and will make it minds inclination if pondered frequently.

Dvedhavitakka Sutta: Two Sorts of Thinking -
"Whatever a monk keeps pursuing with his thinking & pondering, that becomes the inclination of his awareness.

See the tanha sutta as well for craving ref.

OP: would it make more sense setting shorter times which I can finish?

When one does not have Sampajañña, i.e., know there is a sensation and know it is impermanent one is accumulating Sankhara / Karma. 1
In daily activities, a novice generally does not have Sampajañña, therefore accumulates Sankhara.
When one is in proper meditation (not merely sitting on a cushion distracted) one does not accumulate sankhara and also dilutes the effects of past sankhara.
Also during a meditation session, there are times one remains distracted and it might take a while to settle into a serious meditation.
Therefore a meditation session should be sufficiently long to compensate for distraction during meditation and the lack of Sampajañña during daily activities. Short sessions may not give desired results. E.g.

polishing brass takes some time to remove the oxidisation. If you do this for a short time then this will not restore the shine.
to create fire one needs to rub 2 sticks until they catch fire. If you stop rubbing prematurely it does not light up.

OP: Is there such a thing as the momentum of accomplishment in meditation or even in virtuous activity in general? Or, is such a feeling of success a kind of attachment, and problematic?

If one tries to perceive the quality of a meditation session this leads to disappointment or satisfaction. This counters what meditation tries to achieve that is not to be averse or attached.

1

Know the feeling

i. On seeing a form with the eye,

one investigates the form that is the basis for mental joy,
one investigates the form that is the basis of mental pain,
one investigates the form that is the basis of equanimity.

ii. On hearing a sound with the ear,

one investigates the sound that is the basis for mental joy,
one investigates the sound that is the basis of mental pain,
one investigates the sound that the basis of equanimity.

iii. On smelling a smell with the nose,

one investigates the smell that is the basis for mental joy,
one investigates the smell that is the basis of mental pain,
one investigates the smell that is the basis of equanimity.

iv. On tasting a taste with the tongue,

one investigates the taste that is the basis for mental joy,
one investigates the taste that is the basis of mental pain,
one investigates the taste that is the basis of equanimity.

v. On feeling a touch with the body,

one investigates the touch that is the basis for mental joy,
one investigates the touch that is the basis of mental pain,
one investigates the touch that is the basis of equanimity.

vi. On cognizing a mind-object with the mind,

one investigates the mind-object that the basis of mental joy,
one investigates the mind-object that is the basis of mental pain,
one investigates the mind-object that is the basis of equanimity.

Dhātu Vibhaṅga Sutta

Know that the feels are impermanent so do not cling onto them

If he feels a pleasant feeling,

he understands that it is impermanent;
he understands that it is not to be clung to;
he understands that there is no delight in it.

If he feels a painful feeling,

he understands that it is impermanent;
he understands that it is not to be clung to;
he understands that there is no delight in it.

If he feels a neutral feeling,

he understands that it is impermanent;
he understands that it is not to be clung to;
he understands that there is no delight in it.

If he feels a pleasant feeling, he feels it in a detached manner.
If he feels a painful feeling, he feels it in a detached manner.
If he feels a neutral feeling, he feels it in a detached manner.

Dhātu Vibhaṅga Sutta


text:
Inauthentic Compassion and Friendship
When I meditate on compassion, afterwards there is a post-meditative effect of making me kinder, but usually in a way that doesn't benefit me. It makes me want to rekindle friendships that were not desirable in fear that the others would suffer, or give others time and attention in ways that somewhat disadvantage me.
How can this be dealt with?
Is compassion even linked with being friends, or is it distinct; i.e. how can one be compassionate yet retain distance with others?

One should associate with true friends and disassociate with false friends.
One should associate with those are:

(1) He is pleasant [loving]. piyo ca hoti
(2) He is agreeable. manāpo ca
(3) He is respectful. garu ca
(4) He is worthy of respect. bhāvanīyo ca
(5) He admonishes, patient when admonished. vattā ca vacana-k,khamo ca
(6) He is profound in conversation. gambhīrañ ca kathaṁ kattā hoti,
(7) He does not engage us in the impossible. no ca aṭṭhāne niyojeti.

(Piya) Mitta Sutta 2

(1) He gives what is difficult to give. duddadaṁ dadāti
(2) He does what is difficult to do. dukkaraṁ karoti
(3) He tolerates what is difficult to tolerate. dukkhamaṁ khamati
(4) His secrets he reveals. guyham assa āvi karoti
(5) Your secrets he keeps. guyham assa pariguhati
(6) In misfortune he forsakes you not. āpadāsu na jahati
(7) He does not look down (on you) when you
  have failed [are destitute]. khīṇena nâtimaññati

(Piya) Mitta Sutta 1

“Young houselord, there are these 4 who should be known as true-hearted friends:
(1) The helper (upakara)
should be known as a true-hearted friend.
(2) The one constant in joy and in sorrow (samana,sukha,dukkha)
should be known as a
  true-hearted friend.
(3) The good counsellor (atth’akkhayi)
should be known as a true-hearted friend.
(4) The caring (anukampaka)
should be known as a true-hearted friend.
(1) The helper, young houselord, should be known as a true-hearted friend for these four reasons:
(a) He guards you when you are heedless.
  pamattaṁ rakkhati
(b) He guards your property when you are heedless. pamattassa sāpateyyaṁ rakkhati
(c) He is a refuge to you when you are in fear [in danger]. bhītassa saraṇaṁ hoti
(d) When you are faced with tasks, he provides you with double the supplies you need. uppannesu kicca,karaṇīyesu tad
  di,guṇaṁ bhogaṁ anuppadeti
The helper, young houselord, should be known as a true-hearted friend for these four reasons.
(2) The one constant in joy and in sorrow [a friend through thick and thin] should be known as
  a true-hearted friend for these 4 reasons:
(a) He tells you his secrets. guyham assa ācikkhati
(b) He keeps your secrets. guyham assa parigūhati
(c) He does not abandon you in your troubles. āpadāsu na vijahati
(d) He would even give up his life for you. jīvitaṁ pi’ssa atthāya pariccattaṁ hoti
The one who is constant in joy and sorrow, young houselord, should be known as a true-hearted
  friend for these four reasons.
(3) The good counsellor [the one who shows benefits or the goal] should be known as a truehearted friend for these four reasons:92
(a) He restrains you from bad. pāpā nivāreti
(b) He exhorts you to do good. kalyāṇe niveseti
(c) He lets you hear what you have not heard before. assutaṁ sāveti
(d) He shows you the way to heaven. saggassa maggaṁ ācikkhati
The good counsellor, young houselord, should be known as a true-hearted friend for these four
  reasons.
(4) The caring should be known as a true-hearted friend for these four reasons:
(a) He does not delight in your misfortunes. abhaven’assa na nandati
(b) He delights in your good fortunes. bhavena’ssa nandati
(c) He prevents others from speaking ill of you. avaṇṇaṁ bhaṇamānaṁ nivāreti
(d) He commends others who speak well of you. vaṇṇaṁ bhaṇamānaṁ pasaṁsati
The one who is caring, young houselord, should be known as a true-hearted friend for these 4
  reasons.”
The Blessed One said this.
Having said that, the Sugata [the well-farer], the Teacher, further said this:
The friend who is a helper, and the friend in weal and woe,
and the friend who gives good counsel, and the caring friend—
these four are (true) friends, thus the wise should know
and devotes himself with respect as a child would his parents

Sigal’ovada Sutta
At a spiritual level they should have these qualities:

(1) The accomplishment of faith (saddhā,sampadā),
(2) The accomplishment of moral virtue (sīla,sampadā),
(3) The accomplishment of charity (cāga,sampadā),
(4) The accomplishment of wisdom (paññā,sampadā)

Dīgha,janu Sutta
One should disassociate or distance oneself from those with the following qualities:

“Young householder, there are these four who should be known as enemies in the guise of
  friends:
(1) The downright taker,
young householder, should be known as an enemy in the guise of
  a friend.
(2) The mere talker,
young householder, should be known as an enemy in the guise of a
  friend.
(3) The sweet-talker,
  young householder, should be known as enemy in the guise of a
  friend.
(4) The destructive companion,
young householder, should be known as an enemy in the
  guise of a friend.
Young householder, these are the four who should be known as enemies in the guise of
  friends.
(1) The downright taker, young houselord, should be known as an enemy in the guise of
  a friend for these four reasons:
(a) He only takes (without ever giving). añña-d-atthu,haro hoti
(b) With little, he desires much. appena bahum icchati
(c) He does what needs doing only out of fear. bhayassa kiccaṁ karoti
(d) He serves with an ulterior motive. sevati attha,kāraṇā
The downright taker, young houselord, should be known as an enemy in the guise of a friend for these
  four reasons.
(2) The mere talker, young houselord, should be known as an enemy in the guise of a friend for
  these four reasons:
(a) He claims to having been hospitable in the past. atītena paṭisantharati
(b) He promises hospitality in the future. anāgatena paṭisantharati
(c) He worms his way with empty favours. niratthakena saṅgaṇhāti
(d) In present tasks, he feigns misfortune. paccuppannesu kiccesu vyasanaṁ dasseti
For these four reasons, young houselord, the mere talker should be known as an enemy in the guise of
  a friend.
(3) The sweet talker, young houselord, should be known as an enemy in the guise of a friend for
  these four reasons:
(a) He approves of your doing wrong. pāpakaṁ pi’ssa anujānāti
(b) He approves of your doing right [or disapproves of it,
  depending on what profits him]. kalyāṇaṁ pi’ssa anujānāti
(c) He sings your praises to your face. sammukhāssa vaṇṇaṁ bhāsati
(d) He runs you down behind your back. param,mukhāssa avaṇṇaṁ bhāsati
For these four reasons, young houselord, the sweet talker should be known as an enemy in the guise
  of a friend.
(4) The destructive companion, young houselord, should be known as an enemy in the guise of
  a friend for these four reasons:
(a) He is your companion in taking strong drinks, distilled drinks, fermented drinks that which causes
  heedlessness.
(b) He is your companion in roaming (and loitering in) the streets at unseemly hours.
(c) He is your companion in frequenting fairs [shows].
(d) He is your companion in indulging in gambling, a basis for heedlessness.
For these four reasons, young houselord, the destructive companion should be known as an enemy in
  the guise of a friend.”
The Blessed One said this.
Having said that, the Sugata [the well-farer], the Teacher, further said this:
The friend who merely takes, and the friend who only talks,
and the one who sweet-talks, and the companion who brings destruction—
these four are not friends. Thus the wise should know:
they should be avoided from afar like a dangerous path.

Sigal’ovada Sutta
Associating with false friends will influence you to be more unskillful than what you are in a spiritual sense and fail in a worldly sense. Sometimes true friends may seem like a pain when they watch out for you but they are the ones who make you a better person by helping you prosper in a world sence and be more skilful in a spiritual sense.
Also, see:

Spiritual friendship by Piya Tan
Spiritual Friendship: Stories of Kindness by Piya Tan
Bad friendship by Piya Tan

Compassion isn't the problem, and often requires a bit of courage as it kind of puts you in a place of vulnerability. Not everyone has the guts for that.
The other way around, someone feeling inclined to exploit others compassion is the actual problem, not only for themselves, but also for their surroundings. Everybody loses.
For a friendship to work out, compassion needs to be mutual. And if mutuality isn't possible, refraining from being hurtful is probably all one is obliged to do.

About the last part, i know theres a sutta somewhere for this. Can anyone chime in? I can't find it.

Lest they are willing to be trained at least semi-formally it is probably not going to be beneficial enough compared to prioritizing training.

Usually it is not so because real meditation brings insights. Maybe you should meditate more. Real meditation brings a transformation in consciousness. After meditation you can never be the same.
In my experience, it took me quote some time and effort of meditating to finally see that I was fooling myself all the time. What I called meditation was actually thinking. Thinking can never bring the same results as meditation.
In meditation, mind starts to dissolve and you start falling in trance. Meditation is very intense. You must be emotionally strong and intelectually accomplished before you can expect some real meditation. Accomplished, expert thinkers naturally start meditating and are drawn to the life of a meditator. IMHO, all real meditators used to be expert intellectuals. For example, Blaise Pascal became a meditator in after his phase in physics.
Compassion and friendship for all living entities and detachment from mundane life are qualities of an accomplished meditator. He becomes a being of compassion, a friend in the true sense of the term.
Meditation on compassion or Metta is nicely defined in the suttas. There are proper guidelines and qualifications for performing metta. You should read Karaniya Metta Sutta and Metta (Mettanisamsa) Sutta for full understanding of the process. I wish you best luck in your practice.

It makes me want to rekindle friendships that were not desirable in
  fear that the others would suffer, or give others time and attention
  in ways that somewhat disadvantage me.

It could be you're suffering from mild case of Christ complex.

"The term can also refer to a state of mind in which an individual
  believes that he or she is responsible for saving or assisting
  others..." -- Wikipedia, Messiah complex

Even though others are suffering, you're not responsible for their happiness. Rather that trying to save your friends, instruct them to meditate. They have their own life.

Compassion provides benefits to the recipient of that compassion. You cannot exclude yourself from the practice of immeasurable compassion. See AN7.68:

Two people understand the meaning and the teaching and practice accordingly:
  one practices to benefit themselves but not others, and one practices to benefit both themselves and others.
The person who practices to benefit themselves but not others
  is reprehensible in that respect.
The person who practices to benefit both themselves and others
  is praiseworthy in that respect.

This perspective is somewhat surprising to those who have been taught to benefit  others over self


text:
Unconscious Grasping to a Self
In daily life, I guess my self-grasping is not very salient; people tell me I'm considerate, open. However, I've written stories in the past, and in my fiction I project these fantasies that are incredibly grandiose and self-absorbed. I'm not sure what to conclude here.
Is it possible to have an unaware, unconscious self-grasping (which would here transpire in my stories)?
Or perhaps, could writing down and elaborating grandiose, self-themed stories exacerbate self-grasping which would otherwise be much less?
I am somewhat confused about this as, as I said, these stories seem not to fit my day to day personality, but clearly possess important themes of self-grasping.

OP: Is it possible to have an unaware, unconscious self-grasping (which would here transpire in my stories)?

There are 18 internal and external views across past, present and future making a total of 108 views of self rooted in carving.
18 Internal Preoccupations with Craving

(1) “I am”
(2) “I am this [I am like this]”
(3) “Thus am I [I am like that]”
(4) “I am otherwise”
(5) “I do not exist”
(6) “I exist”
(7) “May I be”
(8) “May I be this [be like this]”
(9) “May I be so [be like that]”
(10) “May I otherwise”
(11) “I might be”
(12) “I might be this [be like this]”
(13) “I might be that [be like that]”
(14) “I might be otherwise”
(15) “I shall be”
(16) “I shall be this [be like this]”
(17) “I shall be so [be like that]”
(18) “I shall be otherwise”

Tanhā Jālinī Sutta / (Vicarita) Tanha Sutta
For an untrained person, any externals experience always result in the self-view. What one should do is to contemplate perceptions, thought, view as not-self. To to this one have to develop awareness into this process.

the eye, form, eye-consciousness, eye-contact, feeling, craving, are not-self,
the ear, sounds, ear-consciousness, ear-contact, feeling, craving, are not-self,
the nose, smells, nose-consciousness, nose-contact, feeling, craving, are not-self,
the tongue, sounds, tongue-consciousness, tongue-contact, feeling, craving, are not-self,
the body, touches, body-consciousness, body-contact, feeling, craving, are not-self,
the mind, mind-objects, mind-consciousness, mind-contact, feeling, craving, are not-self.

Cha Chakka Sutta

OP: could writing down and elaborating grandiose, self-themed stories exacerbate self-grasping which would otherwise be much less?

Self-grasping is always there. (Only at streem-entry is this broke.) More you think about oneself (108 through paths above) it is reinforced.
If

perceptions,
thoughts, or
views

do arise one should straighten them by contemplating:

Impermanent as impermanent
Painful as painful
Not-self as not-self
Impure [unattractive or repulsive] as impure

See Vipallasa Sutta
When creating these stories your self-view may be reinforced. If you do this as living maybe you can take a step back and try to write stories without too much self-centeredness. When you have to write something and the above Vipallasa arises contemplate on the antidote.
This and this answer also might be of interest on how to eliminate self-view arising.

Or perhaps, could writing down and elaborating grandiose, self-themed stories exacerbate self-grasping which would otherwise be much less?
From AN8.35, we have the case of an elaborate grandiose grasping by an ethical persion:

The heart’s wish of an ethical person succeeds because of their purity.
Next, someone gives to ascetics or brahmins such things as food, drink, clothing, vehicles; garlands, fragrance, and makeup; and bed, house, and lighting.
  Whatever they give, they expect something back.
  And they’ve heard:
  ‘The Gods of Brahmā’s Host are long-lived, beautiful, and very happy.’
  It occurs to them:
  ‘If only, when my body breaks up, after death, I would be reborn in the company of the Gods of Brahmā’s Host!’
  They settle on that idea, concentrate on it and develop it.
As they’ve settled for less and not developed further, their idea leads to rebirth there.
  When their body breaks up, after death, they’re reborn in the company of the Gods of Brahmā’s Host.
  But I say that this is only for those of ethical conduct, not for the unethical.

Wishes, be they simple or grandiose, entangle us in grasping at the continued existence of identity view, that illusion of a self. Yet even the grandiose story ends. All those grandiose features and details die.

When they know a thought with their mind, they don’t get caught up in the features and details.
  If the faculty of mind were left unrestrained, bad unskillful qualities of desire and aversion would become overwhelming. For this reason, they practice restraint, protecting the faculty of mind, and achieving its restraint.
  When they have this noble sense restraint, they experience an unsullied bliss inside themselves.
-- MN 51

To live without wishes in this very life, extinguished, requires understanding and letting go of wishes. Perhaps your writing is simply a way for you to understand what it is you or others might be holding on to. In that understanding of the inevitable impermanence of the grasped might also be the letting go.

They live without wishes in the present life, extinguished, cooled, experiencing bliss, having become holy in themselves.

OP: In daily life, I guess my self-grasping is not very salient; people tell me I'm considerate, open.

Just because you're considerate and open, doesn't mean you're not self-grasping.
Even if you think "I am considerate and open" and feel happy about that, that's already self-grasping because you're associating some mental ideas to your self.
This can be see in SN 22.59:

"And is that which is inconstant easeful or stressful?"
"Stressful, lord."
"And is it fitting to regard what is inconstant, stressful, subject to
  change as: 'This is mine. This is my self. This is what I am'?"
"No, lord."

However, for lay persons who are not stream enterers, I think recollecting examples of when you were considerate and open, is more skillful than having the three poisons occupying the mind, because it brings some joy to your mind and removes the three poisons.
We see recollection of virtues and generosity in AN 11.13:

"Furthermore, there is the case where you recollect your own virtues:
  '[They are] untorn, unbroken, unspotted, unsplattered, liberating,
  praised by the wise, untarnished, conducive to concentration.' At any
  time when a disciple of the noble ones is recollecting virtue, his
  mind is not overcome with passion, not overcome with aversion, not
  overcome with delusion. His mind heads straight, based on virtue. And
  when the mind is headed straight, the disciple of the noble ones gains
  a sense of the goal, gains a sense of the Dhamma, gains joy connected
  with the Dhamma. In one who is joyful, rapture arises. In one who is
  rapturous, the body grows calm. One whose body is calmed experiences
  ease. In one at ease, the mind becomes concentrated.
"Mahanama, you should develop this recollection of virtue while you
  are walking, while you are standing, while you are sitting, while you
  are lying down, while you are busy at work, while you are resting in
  your home crowded with children.
"Furthermore, there is the case where you recollect your own
  generosity: 'It is a gain, a great gain for me, that — among people
  overcome with the stain of possessiveness — I live at home, my
  awareness cleansed of the stain of possessiveness, freely generous,
  openhanded, delighting in being magnanimous, responsive to requests,
  delighting in the distribution of alms.' At any time when a disciple
  of the noble ones is recollecting generosity, his mind is not overcome
  with passion, not overcome with aversion, not overcome with delusion.
  His mind heads straight, based on generosity. And when the mind is
  headed straight, the disciple of the noble ones gains a sense of the
  goal, gains a sense of the Dhamma, gains joy connected with the
  Dhamma. In one who is joyful, rapture arises. In one who is rapturous,
  the body grows calm. One whose body is calmed experiences ease. In one
  at ease, the mind becomes concentrated.

So, it's OK to recollect examples of one's virtues and generosity.

OP: Or perhaps, could writing down and elaborating grandiose, self-themed stories exacerbate self-grasping which would otherwise be
  much less?

Oh yes, from SN 42.2:

Then Talaputa, the head of an acting troupe, went to the Blessed One
  and, on arrival, having bowed down to him, sat to one side. As he was
  sitting there he said to the Blessed One: "Lord, I have heard that it
  has been passed down by the ancient teaching lineage of actors that
  'When an actor on the stage, in the midst of a festival, makes people
  laugh & gives them delight with his imitation of reality, then with
  the breakup of the body, after death, he is reborn in the company of
  the laughing devas.' What does the Blessed One have to say about
  that?"
"Apparently, headman, I haven't been able to get past you by saying,
  'Enough, headman, put that aside. Don't ask me that.' So I will simply
  answer you. Any beings who are not devoid of passion to begin with,
  who are bound by the bond of passion, focus with even more passion on
  things inspiring passion presented by an actor on stage in the midst
  of a festival. Any beings who are not devoid of aversion to begin
  with, who are bound by the bond of aversion, focus with even more
  aversion on things inspiring aversion presented by an actor on stage
  in the midst of a festival. Any beings who are not devoid of delusion
  to begin with, who are bound by the bond of delusion, focus with even
  more delusion on things inspiring delusion presented by an actor on
  stage in the midst of a festival. Thus the actor — himself intoxicated
  & heedless, having made others intoxicated & heedless — with the
  breakup of the body, after death, is reborn in what is called the hell
  of laughter. But if he holds such a view as this: 'When an actor on
  the stage, in the midst of a festival, makes people laugh & gives them
  delight with his imitation of reality, then with the breakup of the
  body, after death, he is reborn in the company of the laughing devas,'
  that is his wrong view. Now, there are two destinations for a person
  with wrong view, I tell you: either hell or the animal womb."

Well, it's not the same as your case, but it's similar.


text:
Tanhā Jālinī Sutta and Self-Views
This answer by Suminda Sirinath S. Dharmasena noted the self-views, in the Tanhā Jālinī Sutta, that promote clinging to a self.
I wish here to verify my understanding, namely that these views are divided into 5 parts:

(1) “I am”
(2) “I am this [I am like this]”
(3) “Thus am I [I am like that]”
(4) “I am otherwise”

These seem to relate to affirmations in the present, linked to affirming permanence of the self, e.g. "I am like this [always]."

(5) “I do not exist”
(6) “I exist”

Here the two views are about extremes of eternalism and nihilism.

(7) “May I be”
(8) “May I be this [be like this]”
(9) “May I be so [be like that]”
(10) “May I otherwise”

Here, the quality of yearning and attachment is involved, namely through fantasizing.

(11) “I might be”
(12) “I might be this [be like this]”
(13) “I might be that [be like that]”
(14) “I might be otherwise”

Here, it is speculation which is in question, and the contemplation of hypothetical realities which is the problem.

(15) “I shall be”
(16) “I shall be this [be like this]”
(17) “I shall be so [be like that]”
(18) “I shall be otherwise”

Lastly, projection into the future and imagining yet occurred realities is in question.
Are these last five conclusions correct? Or have I misunderstood certain elements?
Overall, I understand this sutta to be divided into sections 1-6 pertaining directly to ignorance, 7-10 as attachment, and 11-18 as linked to the hindrances of doubt and worry.
I wonder, though, how all these separate aspects are all considered 'self-views'; is it because all kleshas mentioned previously come from and are manifesations of the self?

kleshas cannot be manifestations or come from the self, since there is no self in the first place.
What there is is various conditioned things that puthujjanas ''take up'', ie the various ''taking up'' is the upadanas, ie the fuel, and they claim the things taken up is self. They also claim that either it is not possible to stop upadanas, or that if is possible to stop the fuel, then it is bad to stop the fuel.
the buddha says the opposite, for instance

But the well taught Ariyan disdple, brethren, who discers those who
  are Ariyans; who are skilled in the Ariyan doctrine, trained in the
  Ariyan doctrine; who discern the worthy ones, who are skilled in the
  worthy doctrine, trained in the worthy doctrine, regard not body as
  the Self, regard not body as having a Self, regard not body as being
  in the Self, regard not the self as being in the body;
regard not feeling as the Self, regard not feeling as having a Self,
  regard not feeling as being in the Self, regard not the self as being
  in feeling;
regard not perception as the Self, regard not perception as having a
  Self, regard not perception as being in the Self, regard not the self
  as being in perception;
regard not the activities as the Self, regard not the activities as
  having a Self, regard not the activities as being in the Self, regard
  not the self as being in the activities;
regard not consciousness as the Self, regard not consciousness as
  having a Self, regard not consciousness as being in the Self, regard
  not the self as being in consciousness;
do not run and revolve round and round from body to body, do not run
  and revolve round and round from feeling to feeling, do not run and
  revolve round and round from perception to perception, do not run and
  revolve round and round from activities to activities, do not run and
  revolve round and round from consciousness to consciousness.
They, not running and revolving round and round from body to body, not
  running and revolving round and round from feeling to feeling,
not running and revolving round and round from perception to
  perception, not running and revolving round and round from activity to
  activity, not running and revolving round and round from consciousness
  to consciousness are released from body, are released from feeling,
  are released from perception, are released from the activities, are
  released from consciousness, they are released from rebirth, from old
  age and decay, from sorrow and grief, from woe, lamentation and
  despair; they are released from suffering, I declare.

http://obo.genaud.net/dhamma-vinaya/pts/sn/03_kv/sn03.22.099.wood.pts.htm#p1
same thing with the next sutta

The Exalted One was once staying near Sāvatthī at the Jeta Grove in
  Anāthapiṇḍika's Park.
And there the Exalted One addressed the brethren, saying:
"Brethren!"
"Master!" responded those brethren.
The Exalted One said:
"Incalculable, brethren, is the beginning of this round of rebirth.
No beginning is made known of beings wrapt in ignorance, fettered by
  craving, who run on, who fare on the round of rebirth.
■
Just like a dog, brethren, tied up by a leash to a strong stake or
  pillar - if he goes, he goes up to that stake or pillar; if he stands
  still, he stands close to that stake or pillar; if he squats down, he
  squats close to that stake or pillar; if he lies down, he lies dose to
  that stake or pillar.
■
Even so, brethren, the untaught manyfolk regard body (thus):|| ||
'This is mine; this am I; this is the self of me.'
They regard feeling (thus):|| ||
'This is mine; this am I; this is the self of me.'
They regard perception (thus):|| ||
'This is mine; this am I; this is the self of me.'
They regard the activities (thus):|| ||
'This is mine; this am I; this is the self of me.'
They regard consciousness (thus):|| ||
'This is mine; this am I; this is the self of me.'
■
If they go, it is towards this fivefold grasping-group that they go.
If they stand still, it is close to this fivefold grasping-group that
  they stand still.
If they sit, it is close to this fivefold grasping-group that they
  sit.
If they lie down, it is close to this fivefold grasping-group that
  they lie down.
[128] Wherefore, brethren, again and again must one regard one's own
  mind thus:
'For a long, long time this mind has been tainted by lust, by hatred,
  by illusion.'
By a tainted mind, brethren, beings are tainted.
By purity of mind beings are made pure.
Brethren, have ye ever seen a picture which they call 'a
  show-piece?'"[1]
"Yes, lord."
"Well, brethren, this so-called show-piece is thought out by mind.
Wherefore, brethren, mind is even more diverse than that show
  piece.[2]
Wherefore, brethren, again and again must one regard one's own mind
  thus:
'For a long, long time this mind has been tainted by lust, by hatred,
  by illusion.'
By a tainted mind, brethren, beings are tainted.
By purity of mind beings are made pure.
Brethren, I see not any single group[3] so diverse as the creatures of
  the animal world.
Those creatures of the animal world, brethren, are thought out by
  mind.[4]|| ||
Wherefore, brethren, mind is even more diverse than those creatures of
  the animal world.
Wherefore, brethren, again and again must one regard one's own mind
  thus:
'For a long, long time this mind has been tainted by lust, by hatred,
  by illusion.'
By a tainted [129] mind, brethren, beings are tainted.
By purity of mind beings are made pure.[5]
Just as if, brethren, a dyer or a painter, if he have dye or lac or
  turmeric, indigo or madder, and a well-planed board or wall or strip
  of cloth, can fashion the likeness of a woman or of a man complete in
  all its parts,[6] even so, brethren, the untaught manyfolk creates and
  re-creates its body, creates and re-creates its feelings, creates and
  re-creates its perception, creates and re-creates its activities,
  creates and re-creates its consciousness.
Now as to this, what think you, brother?|| ||
Is body permanent or impermanent?"
"Impermanent, lord."
"That which is impermanent, is it weal or woe?"
"Woe, lord."
"But that which is impermanent, woeful, unstable in nature, is it
  right to regard it thus:
'This is mine, this am I this is the Self of me?'"
"Surely not, lord."
■
"Is feeling permanent or impermanent?"
"Impermanent, lord."
"That which is impermanent, is it weal or woe?"
"Woe, lord."
"But that which is impermanent, woeful, unstable in nature, is it
  right to regard it thus:
'This is mine, this am I this is the Self of me?'"
"Surely not, lord."
■
"Is perception permanent or impermanent?"
"Impermanent, lord."
"That which is impermanent, is it weal or woe?"
"Woe, lord."
"But that which is impermanent, woeful, unstable in nature, is it
  right to regard it thus:
'This is mine, this am I this is the Self of me?'"
"Surely not, lord."
■
"Are the activities permanent or impermanent?"
"Impermanent, lord."
"That which is impermanent, is it weal or woe?"
"Woe, lord."
"But that which is impermanent, woeful, unstable in nature, is it
  right to regard it thus:
'This is mine, this am I this is the Self of me?'"
"Surely not, lord."
■
"Is consciousness permanent or impermanent?"
"Impermanent, lord."
"That which is impermanent, is it weal or woe?"
"Woe, lord."
"But that which is impermanent, woeful, unstable in nature, is it
  right to regard it thus:
'This is mine, this am I this is the Self of me?'"
"Surely not, lord."
"Therefore, brethren, every body whatever, be it past, future or
  present, be it inward or outward, gross or subtle, low or high, far or
  near, - every body should be thus regarded, as it really is, by right
  insight:
'This is not mine.
This I am not.
This is not the Self of me.'
■
Every feeling whatever, be it past, future or present, be it inward or
  outward, gross or subtle, low or high, far or near, - every feeling
  should be thus regarded, as it really is, by right insight:
'This is not mine.
This I am not.
This is not the Self of me.'
■
Every perception whatever, be it past, future or present, be it inward
  or outward, gross or subtle, low or high, far or near, - every
  perception should be thus regarded, as it really is, by right insight:
'This is not mine.
This I am not.
This is not the Self of me.'
■
Every activity whatever, be it past, future or present, be it inward
  or outward, gross or subtle, low or high, far or near, - every
  activity should be thus regarded, as it really is, by right insight:
'This is not mine.
This I am not.
This is not the Self of me.'
■
Every consciousness whatever, be it past, future or present, be it
  inward or outward, gross or subtle, low or high, far or near, - every
  consciousness should be thus regarded, as it really is, by right
  insight:
'This is not mine.
This I am not.
This is not the Self of me.'

OP: Are these last five conclusions correct? Or have I misunderstood certain elements?
Overall, I understand this sutta to be divided into sections 1-6 pertaining directly to ignorance, 7-10 as attachment, and 11-18 as linked to the hindrances of doubt and worry.

Your conclusions seem right.

OP: I wonder, though, how all these separate aspects are all considered 'self-views'; is it because all kleshas mentioned previously come from and are manifestations of the self?

All kleshas are manifestations of:

ignorance
attachment
aversion

Imo these aren't self views but is speech which occurs having directed the thought and made an evaluation.
These are verbalizations of craving based on wrong view and inappropriate attention which becomes the inclination due to frequent giving of attention.
'I am like this' ie, i see no evidence suggesting that the [always] is warranted and is to be inferred. The interpretation i favor is that this occurs due to lack of development, simply grasping the aggregates with inappropriate attention and or wrong view.
'I am like this' may well be verbalized as 'I am old' or 'I am a good meditator' etc, etc.
'I exist' or 'I do not exist' are expressive of speculative views about the nature of what is called 'self' in the world.
A person with perfected view and concentration is incapable of thinking along those lines because they never give inappropriate attention and are therefore incable of verbalizing craving such as ie 'i am bored, it would be good to go for a walk' whereas a Sotapanna can still do because he is not perfect in concentration and has work to do in regards to heedlessness.


text:
Responding to Worldly Questions
Namo Buddhaya!
People always ask "How are you?", "Isn't that beautiful/horrible", "You are so lucky/unlucky!", "Did you enjoy/like that", and so on.

How do I respond to these things in a way that doesn't identify with
  the aspects that cause clinging, such as saying my day is good and
  favorable rather than bad or saying I dislike this meal, and so on.
  More specifically, how do I respond to these and other questions like
  so in a way that doesn't push toward a worldly condition such as
  pleasure and pain, status and disgrace, etc.?

Metta!

Conversations may make one feel superior/inferior, good/bad, etc. Your conversation response can be anything within the bounds of right speech (abstaining from lying, from divisive speech, from abusive speech, & from idle chatter). Your mental response should be on account of whatever feeling that arises either pleasant, unpleasant or neutral one should know the sensation as such and that it is impermanent and not worth clinging to.

If he feels a pleasant feeling,

he understands that it is impermanent;
he understands that it is not to be clung to;
he understands that there is no delight in it.

If he feels a painful feeling,

he understands that it is impermanent;
he understands that it is not to be clung to;
he understands that there is no delight in it.

If he feels a neutral feeling,

he understands that it is impermanent;
he understands that it is not to be clung to;
he understands that there is no delight in it.

If he feels a pleasant feeling, he feels it in a detached manner.
If he feels a painful feeling, he feels it in a detached manner.
If he feels a neutral feeling, he feels it in a detached manner.

Dhātu Vibhaṅga Sutta

I don't think regular normal response like: "I'm fine, thank you" to regular normal greetings like "How are you?" would increase or decrease worldly condition like clinging or greed or aversion. About questions like "isn't that beautiful/horrible?", maybe simply telling them the truth that there're always beautiful and ugly aspects to all conditioned phenomena, like a coin would not exist without both faces. Similarly for like/dislike about a particular meal, some people will like it, and others will not; even when it's really a terrible meal, to someone who's been starving for a few days, it's still the most wonderful meal s/he's ever had! This way, not only you give truthful answers but also provide an opportunity for your friend to take a step back and give some further thoughts about the real nature of existence, provided that s/he's a thoughtful person obviously. But even if they're not, there's no harm in any of the answers you've just provided above.

Ideally, I'd consider their meaning and  answer while I try to mindfuly guard for identifing with the aspects that cause clinging. I'd also try to communicate with metta where there is not nessasarily a seperation between anyone or anything at some heart level I would be chanting myself into. Mindfulness and metta together are powerful.

Right Speech is part of the Noble Eightfold Path.

"And what, bhikkhus, is right speech? Abstinence from false speech,
  abstinence from divisive speech, abstinence from harsh speech,
  abstinence from idle chatter: this is called right speech." (SN 45.8)

In AN 10.211 it's explained as among the 10 things that lead to hell:

(4) “He speaks falsehood. If he is summoned to a council, to an
  assembly, to his relatives’ presence, to his guild, or to the court,
  and questioned as a witness thus: ‘So, good man, tell what you know,’
  then, not knowing, he says, ‘I know,’ or knowing, he says, ‘I do not
  know’; not seeing, he says, ‘I see,’ or seeing, he says, ‘I do not
  see.’ Thus he consciously speaks falsehood for his own ends, or for
  another’s ends, or for some trifling worldly end.
(5) “He speaks divisively. Having heard something here, he repeats it
  elsewhere in order to divide those people from these; or having heard
  something elsewhere, he repeats it to these people in order to divide
  them from those. Thus he is one who divides those who are united, a
  creator of divisions, one who enjoys factions, rejoices in factions,
  delights in factions, a speaker of words that create factions.
(6) “He speaks harshly. He utters such words as are rough, hard,
  hurtful to others, offensive to others, bordering on anger,
  unconducive to concentration.
(7) “He indulges in idle chatter. He speaks at an improper time,
  speaks falsely, speaks what is unbeneficial, speaks contrary to the
  Dhamma and the discipline; at an improper time he speaks such words as
  are worthless, unreasonable, rambling, and unbeneficial. (AN 10.211)

It's also mentioned:

“And what is the person whose speech is like honey? Here, some person,
  having abandoned harsh speech, abstains from harsh speech. He speaks
  such words as are gentle, pleasing to the ear, and lovable, as go to
  the heart, are courteous, desired by many, and agreeable to many. This
  is the person whose speech is like honey." (AN 3.28)
“Mendicants, there are these four kinds of good conduct by way of
  speech. What four? Speech that’s true, harmonious, gentle, and
  thoughtful. These are the four kinds of good conduct by way of
  speech.” (AN 4.149)

So you should try to respond in ways that are gentle, pleasing, lovable, and aren't against right speech principles...similar to in metta (loving-kindness) ways.
For the lay people you should respond more in pleasing ways rather than concerning yourself with things like clinging or what pushes towards a worldly condition since such speculations most likely won't lead to anything good.


text:
Jhana Explaination
Namo Buddhaya!
Can someone please SIMPLY explain the EIGHT Jhanas, specifically:

1) What are Jhanas meant to do & why would one want to achieve them?
2) How does one specifically achieve them (instructions please)?
3) What happens in each individual Jhana, from the first to the
  eighth?
4) How can I explain the Jhanas to a newcomer of the Dhamma?

Please use scripture to back up your answers, but don't make your whole answer scripture...
Metta!

where is a duplicate?

I think this was a duplicate or very nearly a duplicate, of a previous topic (i.e. Please describe all the Jhanas in everyday languague). If this question isn't the same as the previous/existing topic, please clarify how this question is different.

the question is very extensive while other questions are very specific to only certain matters

i answered here: https://buddhism.stackexchange.com/questions/2014/methods-for-reaching-jhana?rq=1 because Yuttadhammo answered here.

@Dhammadhatu The banner at the top which says, "This question already has an answer here" -- do you see that has an "edit" link which you can click, to add to the list of questions of which this is a duplicate? I edited this list to add links to the two other topics which you edited just now, but perhaps you too could edit the list if you want to.

Thanks. I will sort out my answers later. I must go now

1) What are Jhanas meant to do & why would one want to achieve them? and 3) What happens in each individual Jhana, from the first to the eighth? are not asked elsewhere. 2) How does one specifically achieve them (instructions please)? is answered in Methods for reaching Jhana and 4) How can I explain the Jhanas to a newcomer of the Dhamma is explained in Describe all the Jhanas in everyday language

I posted an answer to this question here: https://buddhism.stackexchange.com/a/35158/295

@SumindaSirinathS.Dharmasena Well let's see if Dhamma4All edits it somehow. At the moment I read it as, "A simple explanation of what and why and how for all jhanas and each jhana, with references and your own explanation", which is very broad -- i.e. a long answer to do well, maybe a full answer isn't possible, except perhaps by referencing a good book which could answer the question. But IMO anything which could be put in an answer to this question would also fit as an answer to Describe all the Jhanas in everyday language.

1) What are Jhanas meant to do & why would one want to achieve them? will remain largely unaddressed if it put there. I believe this question deserves own answer as putting the answer under another answer makes it out of place. Any way pingback if the question is opened. For the time being, I put the answers under the other question.