Automatically annotating the beginning of my games I play chess online and use an engine to review the game afterwards. This works well when I get out of the opening, but under my current configuration (Raptor GUI running StockFish) I don't get great insight into the beginning of my games. Instead of using the automatic annotation I end up stepping through the first couple moves using a free online openings guide. There are two drawbacks to my current system:


Manually reentering my moves through a the web interface is a little painful
I could use a larger opening book and more detailed comments


Is there a tool (free or commercial) that will provide this? Bonus points if it runs under OS X.

I've looked at the offerings from another question on annotation, one that's not focused on the opening. It looks to me like Tarrasch will tell me what the book moves are, but not tell me much about them, and Arena does something with opening books, but I can't tell what. These are PC applications so I'm basing my comments only on the websites.
As far as I know, all the tools available today offer an opening book (tree) that has to be traversed manually by clicking yourself forwards and backwards in the book. To evaluate the position at every point of the opening, you can have an engine running and combine this with the statistics that are included in the opening book for white win / draw / black win. Relatively recently, Chessbase Online entered the stage. Let's not forget about Chess dot com and Chess 365 who also offer online books. So instead of having a software installed on your computer, you can use these online services to check and evaluate your openings.

Additionally, you could consider posting opening related questions here on Chess SE and get some valuable insights...!