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I think it is impossible to tell without actually seeing the cars and, if they pass your visual inspection and test-drive, a good PPI. Only a close inspection can tell you about prior body damage; heck, even a number of small door/fender dings and paint scratches can detract significantly from the appearance and value of the car. You also need to look at prior maintenance records: oil changes at intervals shorter than recommended by the factory are not only a good sign, but something which most believe will result in reduced risk of IMS bearing falirure, etc. Furthermore, especially as one approaches around 60,000 miles, a number of components can need replacement - e.g., the water pump, serpentine belt, control arms, water reservoir, clutch, MAF sensor, etc., etc. Have these already been replaced?
How hard was the car driven? A dealer can tell if it has been over-revved at some point and other visual clues can also help - are the rear tires showing excessive wear consistent with burn-out starts, how does the clutch/shifter/transmission feel/ is there a history of early clutch replacement? What about the rims - do they show excessive scuffs and scrapes, consistent with careless operation? How does the owner present? Is he/she a knowledgeable Porsche fan, or some young kid who knows nothing about them but bought one because it was a chick magnet? And where has the car been serviced and with what type of parts? Has it been serviced at a recognized Porsche shop, or by some unkown mechanic who has muddled his way through?
On the debate concerning years and the 2.7 versus the 3.2, I would pay much less attention to this than the condition and maintenance history. Yes the S has more horse power, torque and another gear in their manual transmissions. However, my 2000 2.7 has plenty enough power and torque for my purposes. I am still able to exceed our legal speed limit in second gear and have no interest in engaging in stoplight grand prix behavior. Of course, in the past I owned sports cars that were clearly underpowered (including a couple of Fiat x/19's), but loved them nonethless because of the handling and precision. In that regard, it is worth noting that while the glass window of the 2003 and later Boxsters was more practical, it also added a significant amount of weight precisely where you don't want it - high up! Remember, even in Formula 1 cars, the small amount of fuel burned per lap reduces weight sufficiently to reduce lap times by about 1/10th of a second - and that is weight that is carried very low in the car!
My suggestion is that you purchase the car in the best condition with the best maintenance history and which has a colour scheme/options that you can not only live with, but enjoy over the period of ownership.
Good luck!
Brad
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