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I was in a similiar situation a few months ago and drove both an'03 and '02S. I ended up going with the S and love it. The added power and red calipers sold me. I can always upgrade to a glass top later.
There seems to be a good bit of Boxsters out there so be patient and try to find one with low miles and records. Easier said then done...huh?
As far as repairs go I do not know but scheduled maint. is way cheaper if you avoid a dealer.
Good luck,
Jeff
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