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My experience is that cars either nickle and dime you or they don't. When you find one that doesn't, keep it, because it likely won't start.
On the other hand, cars that always seem to have something wrong seem to always continue to need something. Those are the worst cars - because you'll sink $5k into sorting things out and then want to get rid of it because you are tired of it nickle and diming you...but you MAY have gotten it sorted out, or maybe not.
My recommendation is to keep enjoying the boxster. It's fully depreciated, or just about, so any repairs at this point are going to be cheaper than the depreciation hit you'll take by itself with any newer car.
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99 Boxster 5spd - 64k miles
06 Civic SI - 114k miles, D.D., unbelievably reliable and fun to beat on everyday.
08 Legacy GT 5spd - 74k miles.
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