Gen1 Insight, throw some money at the suspension and brakes and maybe a CAI (if anyone makes one for the insight) and then put some nice grippy all seasons on either the stock rims or something subdued/not-obviously-non-stock thats fairly light? Alternately, Clubman S with any usual mild mods, a set of 17x7" Rota RBs wrapped in a good all-season, and the rear pillars (on the "barn door" rear end) painted to color-match the body color up to the bottom of the rear side windows, then painted black from the bottom to the top of the rear side windows, then color matched to the roof color. Might be more $$$, but definitely faster and likely more fun if set up correctly, and can still haul some stuff if needed. Plus... its a mini 
With 20K you could make something really cool, really custom. Why not rock a Volvo 240 with a factory fresh, highly muffled LSx motor and T56? You could have a shop build you one for less than 20K and it would be way cooler than any new car for 99% of people.
Hey, if doors/seats don't really matter, how about an FR-S/BR-Z? Doesn't look too cheap, and the Subaru or Scion badge is non-offensive to people who'd see it as conspicuous consumption, plus anybody who knows what it is will probably think it's cool.
Jaynen
HalfDork
10/4/12 10:40 a.m.
CTS-v Is a pretty good option if mpg isnt a big deal. It's a cadillac so it doesnt come off as snootie as a german vehicle, probably easy for people to get into, should have space
SVreX
MegaDork
10/14/12 12:33 p.m.
I'm not looking too hard. Per my initial post, it's a little theoretical for now.
Don't know if this was mentioned, I just skimmed through the other pages, but how about a nice 03-04 Nissan Maxima SE? 3.5 V6, 6 spd manual, fun to drive yet still classy.
Somewhat related - drove up through Jasper/Ellijay this weekend and was surprised at the number of MINIs around and for sale at the local dealers. Who knew?
