I just sold my S.
I had it for exactly 6 years, and put 60,000 miles on it. I paid more to maintain it than a "normal" car, but not that much more. In the end, I sold it for $12K less than I bought it for. That is $2K per year. You can't even buy a new Honda Accord for less than that.
IMS bearing? Frankly, I didn't worry about it that much. It certainly wouldn't keep me from buying a 986.
I get the sense you will have a hard time enjoying this car if you think it's about to fall apart every time you drive it.
It's pretty simple: Buy it. Maintain it. Drive it.
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SOLD - 2002 Boxster S - PSM, Litronics, De-ambered, Bird Bike Rack, Hardtop, RMS leak...
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