I've had a good time at GaryCon each time I've been.I am going to Adepticon which moved to Milwaukee this year. I was thinking maybe taking a week from work and doing Gary con too, but folks are not making it sound very nice here.
It's a smaller convention. The dealer hall isn't nearly as immense as GenCon (or Origins, even). The amount of games isn't huge, and it's mostly focused on older games (or OSR-style.)
But it feels like a family reunion with the cousins you used to play D&D with. It's self-contained within the resort (unless you want to visit the historic sites). Servers will bring you beer to your gaming tables.