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2001 S
I bought a 2001 S this past May for $28,000 but it only had 7,600 miles on it. Last I looked 27K is the KBB for excellent condition and I think you could actually get it for 25K so I'd start at 24K or 23K and work up to 25K.
I highly recommend that you get the car inspected by a Porsche dealership to ensure that the rear main seals are not leaking. The RMS leaks will cost you $800 to repair.
Luckily my car is in perfect condition which is why I paid an extra $1K over the KBB.
The car is fun but not as fast as a 911. You can find 1999 911 convertibles with 30K miles in the 30-35K range but I have no idea on your budget.
Good luck!
-Chitowndad
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