I'm in the know and close to chicago but can't get to the city very often. Also I'm not sure I'd be very much help because I rooted when I had 2.1 and not when the OTA for 2.2 came out.
Have you guys read all of the how-to's on here? They are very good and that's what I used to root. I had no previous experience, and the people on here are VERY helpful.