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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.
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2004 550 SE #1081 of 1953 (sold)
1997 911 Targa (sold)
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