I could have opted for a Boxster S that was three or four years newer but the mileage was higher. So I decided to go for a just out of warranty four year old that barely avearged 2400 miles a year. I think I made the right call there.
A saw a few one or two year old cars had more than 10K annual miles and decided to skip a car that was a year round daily driver. I think these should go to the bottom of the list.
Some argue that the 2000-2002 intermediate shaft design was better than the revised version. Nobody really tracks when those fail (car catastrophe) but at one point Consumer Reports was recording consumer complaints and the 00-02's were receiving the lowest number of issues for the 97-2005 period. But who knows how accurate that is. I've put nearly 57K miles on my 2000S and have only had one repair that cost more than $200. Pretty amazing. It also depends how you drive. I always wait for the oil temp to go up before letting the the RPMs go over 2000. I try to use the brakes as little as possible by using the throttle smoothly. Since gas had its little trip into $5 territory I have learned to drive at the speed limit with the car in the 6th gear as soon as possible to go easy on the engine.
also, check the bodywork closely. Painting these cars the right way is not cheap.
I had my whole front end repainted and it was a real job to find a body shop that had enough high end cars but weren't charging high end rates. Fenders, hood and my GT3 bumper done for $1100. Most places wanted closer $2000-$2500 but I managed to get my way, the other partner at the bodyshop was pissed when I picked up the car
p.s.
In this economy get the S. They're practically giving it to you for no extra charge.
Also in my opine and after driving a 2.7 and a 3.2, a car of this curb weight comes "alive" out of corners at about the 240-206 hp mark. Drive an S2000 for comparison. If you can't find an S keep looking. This car should've had a 3.6 from the start because it's really a Carrera roadster in my book, but for political reasons at Porsche they decided to make it a 2.5 and give it a different name even though from the doors to the front bumper it's 99% a 99-01 Carrera.