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It comes down to your priorities and your budget. The Boxsters have been very solid cars and are well-built. High mileage isn't necessarily a problem but get a good PPI on any Boxster you might buy. Better to go to an independent shop that specializes in Porsche for a more thorough inspection. If it checks out on the PPI and you don't have impending clutch, water pump or brake replacement then you can trust the car.
Aside from that, and factoring in your budget (whatever it is):
-'97-'99 was the original Boxster with the weakest engine. Some thought it was a few HP short.
-'00-'02 was basically the same car with a few more HP.
-'03 (I think) got upgrades to the interior materials plus another engine bump if I recall correctly.
-'06-'08 is when the 987 came out (redesign with new chassis) and is a good range to shop for a great car. You'll be in the $20-$30k range, though.
I may be off on some of the timing but these are the groups I'd look at to figure out where your budget puts you, then just look for a clean car with a good PPI. If that $10k number is what you're looking at then I'd target '00-'02. You might have a challenge shopping in MI, though. You could get one from a warmer state and find more inventory.
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