Location
All of the locations are equally workable for me. But really, none are better than NY or ON. I'd prefer ON though. Same as Mike, more or less.

Month
I think we should shoot for late summer to get the most people. Not too late though. WC2004 missed some people due to school. I would say Early August would be the best time.

Days
I think this definitely needs to be a 4-day thing for the "main events". Maybe have people arrive on Sunday, get things going Monday-Thursday, then leave on Friday. If there's a lot of demand for it, 5 days would be good too, but almost a bit excessive.

Activities
I think we shouldn't try to repeat the same things we did at WC2004, though a theme park would be great. Tick was suggesting a concert, and I think that idea would be good too. Or a movie, or bowling. A LAN party would be amazing, but hard to organize. I'd support it if enough people want it though.

Funds
I have no idea how much this trip will cost me, so this is up in the air. Definitely at least a few bucks though. We'll see.