Papal blessings via alternate media? When I went to World Youth Day in 2005 (wow, long time ago now) my wife and I were sick of walking and wanted to enjoy our honeymoon for a bit so we watched the Pope come into Cologne on a boat.  We were with a big group of pilgrims and most of them went but one consoled us saying said something to the effect that, the Pope's blessing extends to those who watch him live on TV.

My question is, and I don't want to delve into scrupulosity here, but how out of sync can live TV be, does taped delay count?  How about watching taped benediction or Mass on EWTN?

And, yes, by count I do mean time off purgatory.  :)
I used to listen to the Vatican Radio podcast which included a recording of the Pope's Urbi et Orbi blessing and they would put a disclaimer in the recording that the blessing didn't apply to recordings, only to those present or watching/listening live.  The key distinction is live versus a recording; even if you're watching the EWTN web stream -- which might be broadcast delayed up to a minute or more due to the nature of "live web broadcasts" it still counts as live.

As for how much it counts toward time off of Purgatory, there is the rule in moral theology that you only receive the graces you're disposed to receive.