I have thought about it, but I don't have the reach of a personal network or time to chase around deals. However there are a lot of people in the far out burbs of Chicago that have some nice stuff, but I would need to make a weekend, or take a day off work, and cruise around. I know I helped a member on here score a deal on a Trek 600 a few weeks ago. I would have bought it had it fit me.
The problem with big cities, and Chicago especially, is there is a lot of people who live in the city and flip bikes easily because there is a market there. I live on the out skirts and there isn't much here, and when their is people ask big $$ for a bike that isn't even worth it. I saw a guy at a garage sale selling a lugged frame Schwinn with lots of rust, needing tires/chain/complete overhaul for $300. I offered him $100 after pointing out what it needed and he responded that he would keep it till some "schmoe" bought it for what he wanted.
I drove away.
So I turn wrenches on cars instead to support my "habit"

But the cold sucks for working outdoors.