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The s2000 is only fun if you're really beating the carp out of it.
the boxster is fun even when it's off.
the interior of the 06 (o5+) looks nothing like the interior of the 00-02 on the boxsters.
it is quite easy to add a single din stereo to any boxster pre-05.
but, there is an ipod/aux cable that you can get that will plug right into the stock stereo.
for the price range you're looking at. (20-25k) you should consider getting a lower milage 00 or 01 boxster S. and 02 in that price range will likely have way higher miles and is really not too different from the 00 or the 01. the cupholders up until the 03 were/are abysmal. the 03-04 are slightly less so.
i think you'll have fun with either car. and if you like running around at 5k+ rpm all the time, the s2k isn't too bad. check out dyno charts on the cars though. the s2000 engine is like an on/off switch. below 6k you have about 110-120 lb/ft torque to the wheels. above that and you have maybe 165.
the boxster S (which has less hp/tq in 2000,2001 and 2002) pretty much always has at least 180-ish lb/tq at the wheels from almost anywhere in the powerband.
note these figures are at the wheels. the specs and mags usually quote at the flywheel.
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