That would be so much fun! I'd go. I know that they have one on my Sugar Glider board every year. They get a few hotels and everyone stays around the same spot. They also have a few "speakers" and "boutiques" (people with online stores set up and sell a little), of course food, and LOTS of hanging out talking.
I think if you made it in a year and really organized it and got a good place for all of us to stay we could save up money and really do it.
SOUNDS LIKE FUN! I kind of vote Chicago too. It seemes really central.