I've made a couple of these before and they always spur up some good conversation...
Requirements: Fun to drive, manual or automated manual trans, back seat able to accommodate the occasional child seat or child, under $20k, I'm gonna put a LOT of miles on it.
Difficulty: No silver cars (lol good luck) and must have black leather.
I've never paid another person to work on my vehicles aside from stuff I don't have the tools to do like tires and alignments. I will do all the work on whatever I buy myself and have a background in german cars. Maintenance cost isn't really a factor here but huge $$ common failure parts should be mentioned.
The contenders:
E46 M3 coupe.
These are starting to drop into the teens around here. The SMG trans may be a ticking time bomb but doesn't scare me. Expensive oil changes. I hear stories of trim failures and various BMWish problems ie. door actuators, suspension bushings, and stupid electrical stuff. Should be a hoot to drive everyday.
E46 330i ZHP: Harder to find than the M3 for about the same money. I still like them.
E39 M5: These are in the teens as well now. Supposedly super maintenance intensive but I don't really see why they should be. Aside from the regular BMW stuff they should be super solid cars. May even be able to steal one with the ZOMG$$ secondary air system failure which doesn't actually effect anything. How can you go wrong with a 400hp V8?
E39 540i Sport Six Speed: Like the M5 but down about 100hp and ten grand. Aside from buy-in I don't see how one of these would be any cheaper to own than the M.
Acura TL Six Speed: Not as nice as the bimmers and front wheel drive, but much newer with fewer miles for the same money. Much less likely to have been enthusiast owned and maintained though. Still a sharp looking car and may be slightly less of a pain than the germans.
Mercedes-Benz E55 AMG Yeah, it's an auto but a damn good one and I'll make an exception here. I don't really know anything about these. Relatively stealthy looks and clean lines. Without the badging you'd be hard pressed to tell it's fast.
Pontiac GTO: Aside from looking like a cavaliers butch older brother these a pretty neat cars. Should be the most reliable as well. Also the best highway mileage of the bunch.
Mazdaspeed 6: Cheapest of the group, only one with all wheel drive. I hear bad stories about turbo seals and motor mount failures.
Any other suggestions?