Part of Winning the PAX East game has to be knowing what PAX is, where it comes from, and why it exists. Answering these questions to my satisfaction would demand a wall of text that would inevitably cause you to bust out your 3DS in the middle of it and just start farming. These links will have to suffice.
First, I recommend that you check out these episodes of Penny Arcade: The Series:
PAX East 2010 - A look behind the scenes at the first PAX East
Mike & Jerry - A personal conversation with the two guys that created Penny Arcade that reveals how, through PAX, they were able to bring together a world of folks that didn't fit in, and give them a community of their own.
PAX East 2012 - Take a brief look at last year's PAX East and get a little more insight into how Penny Arcade and PAX have both had a profound impact on the lives of so many of us.
Even if you're already here, take the time to watch them at some point. They will absolutely enrich your PAX East experience.
As an appendix to Troy's segment, I found this comprehensive list for PAX-related nightlife.
“What PAX makes so very clear is that all of the aggression and all of the controversy and all of the conflict that you see online...all that, when you get into a physical space with people...it all just sort of melts away. I’ve always described PAX as a celebration of the culture, but in that regard it serves another purpose...it reminds me of the humanity of our culture...and it’s becoming more and more important to me as far as that role that it fills.”
-Robert Khoo, Show Director