[mts]

I owned a 2005 S2000 before picking up my current Boxster S. For me:

S2000 > Boxster S:
-Reliability hands down
-Maintenance costs hands down


Boxster S > S2000:
-Cachet
-Day to day driveability/handling

Lots of other things are plus/minuses in my book depending on what you are looking for. An S2000 is a track weapon in the hands of a talented driver, but it will bite you. The Boxster S can make a bad driver look pretty good, it's much more balanced.

Given all that you listed in your original post I would seriously consider the S2000. If I didn't have relatively deep pockets I would probably still have the S2000 instead of the Boxster S.