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Buy the youngest, low mileage S you can find. I'd take a low mileage stock gargage queen over a modified high mileage boxster any day. If you have not driven an S, you should do so before settling on a non-S.
I have a basic boxster and its underpowered. I always see S's around and wonder how much better it would be if I had waited.
I also wish I had bought some guy's garage queen instead of a third hand daily driver.
Prices? Go to a good bookstore and buy a copy of Excellence. The most recent issue has an excellent market report on what to look for, and current prices.
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