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From a lot of research for my own personal needs - I've come to the conclusion that at least for me, the 2006 and 2007 Boxsters are the best. 2005, unless you plan to do the IMS upgrade, are to be avoided as they seem to have the highest cases for failure. I have rarely if ever seen a 2006+ that had a failure.
Case in point: My 986 I had bought for around $13k, and in great condition at 54k miles. But very quickly the plastic window started to deteriorate, and I felt that I wanted to also do the IMS. These two items alone, along with some minor maintenance, and I was approaching the $4k mark quickly. A newer Boxster will eliminate at least the IMS and plastic window issue right off the bat, and they are now in the high teens and lower $20k's for a decent example.
Anyway, it's a matter of paying now or paying later: A cheaper Boxster may need some items a newer one will not.
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