Which Boxster S would be a better purchase in the long run?

[chamilka]

It is really depends on your budget at the end, I think you have to evaluate risks vs rewards. Advantage of buying form a private party is that most times the service history of major upgrades such as IMS will be available. Cars which are sold at the dealer joints do not convey Previous Owners’ service records (due to privacy law) other than what you see in carfax. I have bought really cheap Porsches from rundown dealerships and have had good luck. At the same time I have bought well cared Porsches from private owners and have had bad luck. Having owning many Porsche I always have a fallback strategy ($$ )in case something goes wrong. Higher the risk higher the fallback cash amount . A PPI (a must) only will show you the obvious stuff but not things like IMS or stuff about to go wrong mechanically so it’s not bullet proof but essential.
Some private parties just testing the waters with higher asking price than the true market value so there is always room for negotiation. Low millage cars are more expensive but I am not completely convinced that they are necessarily good deals. You might get a Boxster with 40K miles and inherit all the things about to go wrong, in addition if you end up putting more miles there will be higher deprecation when you sell. on the other hand a high millage car might have all the issues already surfaced out and fixed, and the price has already deprecated a lot so no worries when you sell back.
If you are looking for a low budget car, look for a high millage Boxster sold by private party with all important service records (IMS, RMS, Clutch work).
If you have a high budget, then get the most affordable latest car with lowest miles possible.
Hope this helps

[hamburglar]

With both of the two particular cars in question, I'm not sure either is a great buy. Both have clean CarFaxes, but the 2000 has had six owners so who knows what kind of care each put into the car. In regards to the 2003, I asked the seller, who has been the only owner of the car, how often he changed the oil and what kind of oil he used. He said he's only changed the oil like 4 times. That concerns me to only do an oil change 4 times in over 10 years and waiting 10,000 miles in between oil changes on a Porsche. Best case situation would be that he plans to do a 5th oil change when he hits 40,000 miles, but that would still be once every 8,000 miles.

I think I had narrowed the search to either a 2000 S due to the lowest weight and IMS issue with the later models, and a 2003 S because that's the year that had the best performance of the 986, at least according to my research.