This is an excellent idea to do something about the problem, rather than discussing it from 50 different angles.
We're passed the discussion point and it's time to try different approaches - i think Mark's idea really has a future. It just needs a way to get some resources to get off the ground. Given that we're in SF, a place with both one of the highest density of rich people and having one of the highest homeless populations - it's in an appropriate place and time to take off.
last year i was also on the bus. in summary - it was a blast, but let's put it this way: in big part it was thanks to the bus that i've moved out to the bay area from the midwest.
let's get some more people from chicago to sign up on www.startupbus.com and then get sponsors from the area engaged. contact startupbus sponsoring team and we'll work to make that bus possible.
yeah we need some love from chicago. i am actually from chicago originally, now helping organize startupbus, so i'll do what needs to get done. let's get a chicago bus rolling!