I bought a 99 /Boxster two years ago. Over that two yearsI've spent a grand or so on catching up on the previously neglected maintenance program. I've also spent a bucket of cash on upgrades and improvements, but that was totally discretionary and irrelevant to this discussion. Except for a punctured clutch line, I have not had an actual mechanical failure or CEL to date, so I would have to call this car highly reliable. In fact, I don't think I have ever owned a car this long without some kind of mechanical failure.
These cars are very easy for joe average to work on, and don't cost much to repair if you do your own work and source your parts carefully. The 99 has a dual row IMS bearing, so that should give you some comfort.
You should also keep in mind that forums like this one can give a distorted view of a car's reliability as it is mostly the people that are having problems that post. You rarely hear from the thousands of happy owners that never experience a major problem.
When it comes to sheer driving pleasure, this car has few equals. My advice would be to buy it, enjoy it, learn as much as you can about its mechanical systems, and don't lose sleep over what might go wrong because there's a really good chance you won't have any major issues. Even if you only keep the car a short time, at least you can say you owned a Porsche during your lifetime, which is better than saying that you wish you did when you had the chance. One more thing checked off the bucket list.
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'99 black 986
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