Alright, heres the deal, I want to learn how to true wheels and overhaul bottom brackets. I'm willing to drop some cash on buying tools, including a truing stand, but I need somebody to teach me how to do these things. Nobody I ride with knows how to do these kinds of repairs. Does anybody know of any workshops in Chicago that could teach me how to these things, or alternately, can I persuade anybody to teach me with offers of 12 packs of 312? Let me know.
Share a sixer with ChicagoDave and have him teach you; neither of the things you mentioned are terribly hard, and they're both fun. Pre-bikeforums, I posted for trade in craigslist for someone to teach me things in exchange for a DVD of music. The guy had been a wrench at Cycle Smithy, and I learned a lot.
FYI, Dave likes good beer. Buy him some alpha king or some Bells and he'll be your friend forever.
It really isn't too hartd on either counts. ParkTool.com and Sheldonbrown.com both will inform you of everything you need to know. Truing stand = $40 at Performance and worth it (built two sets of wheels now) and BB tools are always useful.
But I'll second having someone show you and West Town is a great place to get your know-how on.