Debating first Boxster purchase - advice appreciated

[rdc01d]

Hey folks,

Been lurking the forums for 2-3 months now, and am close to purchasing a 1999 Boxster (black on black).
It is just shy of 32K miles, being sold by the second owner.

When I saw it today, I was blown away by how fantastic the condition is, especially the interior. Even with the low miles, on an 18 year old car I would have expected it to look way worse. The car has clearly been taken care of. The current owner has only put about 3K miles on it over the last 3 years.

I'm sure I have read entirely too many website articles, forum posts, and random internet musings, and am a bit freaked out by what may or may not happen with the car. The largest concern being the IMS bearing. I spoke with the local dealership, and they will do the PPI for $300, plus additional cost for an oil change that will include some method of measuring the draining oil using a magnet, and cutting into the old filter for inspection. After mentioning this to the seller, he offered to pay for the oil change portion, since that is not included in the PPI.

I'm logical enough to not do anything in terms of an offer without the PPI from the dealership, but now I feel like I have over-analyzed to the point of not even wanting to buy it!

A family member is a huge car guy. Used to run a successful garage (that he sold), and he has owned and driven everything you can think of (Lambo, Ferrari, Vipers, Mustangs, Vette's, Lexus, BMW, Porsche, Mercedes ... you name it, and he's probably owned it.) When I asked his opinion he said no way to anything almost 20 years old and German. Equated it to playing Russian Roulette. One thing can go wrong and it may cost $2500. I take his advice seriously, so I'm even more hesitant after that conversation.

Aside from a few minor imperfections on the car, and the rear trunk shocks not holding the trunk open on its own, there doesn't see to be anything wrong with the car. Took it out this afternoon (not for long, never got out of 3rd gear) and it sounded great, handled great, no noises, had the top down and it was damn fun to drive!

Am I being way too analytical? This is my first foray into real sports car territory. Last 'fun' car I drove was a 2002 Acura RSX Type S, then once the family started it was 4 door sedan territory. Should I just pony up the $300 for the PPI and then make a decision based on the dealership's opinion? Should I find an indy to do the PPI instead of the local dealer? Am I freaking out over the IMS problem that probably exists in a small percent of the population? I don't really want to spend $10K on a car that needs another $3K maintenance before I even get to enjoy it.

Someone talk me off the ledge!

And by the way - great forum around here, I've gotten tons on info from the sticky's on Thinking about Buying and the sources of information that NickCats posted. Thanks to you all for being so helpful!