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i bought the wife an 07 cayman tiptronic. The only problem we had was a bad water pump at 40k. I changed it myself with a couple of hundred in parts. wasn't really that hard to work on. It was not an S, and felt a little anemic. BUT i had my 996 turbo at the time, so anything else is going to feel slow.
I would love to pick up an 06 or 07 cayman S with a little bit higher miles for a little play toy. You can find them sometimes with sub $20,000 price tags.
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