Get the Boxster S!!! It is hella fun. Also make sure you get the convertible
. But seriously, I've never ridden a s2000 before but it's a honda as someone said. Get the car with attention. The one that people look at and say "that guy has class." To me it's a no brainer. Also, as far as parts and repairs go, just do it yourself. It will cost less than half if you don't pay for labor. And seeing as how you wouldn't ride it that often, you should have time to fix up stuff. You also get an amazing sense of accomplishment.
Having said all that, it would be cool to have a push start...