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Same basic boat, recently purchased a 2000 Boxster S. Here's my opinion:
There are a ton of these cars available. Many have had extensive repairs and upgrades. The year/mileage of the car was less important than the repairs and upgrades.
I found a high mileage car, but with a rebuilt engine, LN IMS bearing upgrade, new clutch, new lower control arms, new rear bearings and a new top with a glass back window w/defog. Make sure you get the records for the maintenance, upgrades and repairs. I got a 12 month/12K mile warranty on the engine. I passed on a bunch of cars because they had NO records. Don't take a car salesman's word for anything...
I have driven the car almost 5K miles since I got it in July and so far, so good. It needs a few details, but I don't mind my 90 mile commute nearly as much. Looking forward to cooler weather so I can drop the top more.
$10-15K will get you a very nice example. Less than that and you are probably taking a chance. There are plenty of Boxsters that are less than $10K, but you will be hard pressed to find any maintenance records and they usually have obvious problems like a CEL, or the top not working.
Beware of buying a "bargain" Boxster with a problem. There are few "bargain" repairs when your car has PORSCHE on the front...
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