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Buy the newest S you can find with an owner who cared for the car and has all the maintenance records. If you drive a base and an S you'll see why I would never again buy a non-S Boxster. It's simply underpowered in my not-so-humble-opinion. (no offense to RaisedOnPorsches car for sale!!!)
The 2007 S model is a great car. 3.4 motor, upgraded interior, glass rear window, good power.
I would not buy a 2002 or older car just because the build quality gets worse and worse the older you get, and the 2003's and up had the all-important rear glass window you don't have to get out of the car half way through the dropping process to make sure the plastic is creased just right.
Whatever you do, don't buy a "fixer uper" that someone has abused or ignored or both. It will be the worst experience you've ever had car-wise. I have dumped more money into my car to get it looking good and running well than I want to admit, and it's still a freakin' $8,500 base Boxster. Ugh!
I would get an indy shop that specializes in Porsches to do your PPI. AND I'd get a 4 wheel alignment on the car I'm about to purchase just to make sure it hasn't been wrecked and can't be brought into solid green alignment. These cars experience a lot of subframe damage when they're slammed up against a curb sideways (out of control driving on streets is to blame) and the owners will just change out the rims and sell the car or keep driving it. An alignment is a cheap $100 insurance policy that you didn't buy a real shiny POS... LIKE I DID.
Best of luck on your search. Remain picky and an amazing example will present itself for very little money. I love the Boxster. Incredibly fun to drive, looks great, and is very forgiving on the track.
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