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Buy the 2010. The common advice is to buy the newest car you can afford. You will be way under water at $18K for an 00S. The cars are similar performance wise. The 10 will be ready to go now vs the 00S having significant down time while you have someone fix the issues.
I just sold an 09 base Boxster w/ 28K mi in the price range you suggested for the 10. You are defn in the ballpark with your est.
CPO - is the 10 at a Porsche dealership? If it was a CPO car and now being sold by a non-Porsche dealer, the CPO is no longer good. However, if the dealer CPO's it, they will be less likely to drop their price since they had to invest ~ $2K to CPO it.
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GPRPCA Chief Driving Instructor
2008 Boxster S Limited Edition #005
2008 Cayman S Sport - Signal Green
1989 928 S4 5 spd - black
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