Legendary car 
1997 BMW M3 Coupe 2dr Coupe
Best handling car
 When I bought this car new in 1997, itwas the fastest BMW 0-60 (5.5 as a standard, modified to 5.3 with Confortichip, B&B Tri-Flo exhaust and Dinan air intake).  It was later voted "Best Handling car in over 30K group" (beating out the Porsche, etc), Car of the year 3 years in a row, '95-'97 (Car andDriver).  Maintenence is high in terms of tires, clutch, brakes and mods, but other than that, nothing major.  The engine was compression tested at 110K and was like-new according to the mechanic (I recommend a small, local, specialized mechanic).