As for cheaper (read mid-ranged) places to eat at Gen Con, I've found the Colt's Grill to be under the radar of most attendees for some reason. It caters to the gamers (video game room, sci-fi and fantasy movies playing, cosplaying waitstaff, and they were even giving away custom dice last year), has pretty good food (their pretzel appetizer was great!), and has never been very busy when I've gone there (about 5 times in the last two years). For a place that is only a couple blocks from the ICC it seems to be a pretty well kept secret.
And I still haven't heard from my wife when she thinks we want to leave Sunday. So I may or may not be able to make it.
I hope to see some of you guys there!