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Congratulations (In advance) - you will NOT regret owning and driving a Boxster. Given your budget, you will probably looking at 2005 or earlier. I highly recommend getting an S - the performance upgrade is well worth any extra $$. I elect to have a very well qualified local independent Porsche shop do all the maintenance. With that approach, typical annual maintenance costs (which my experience supports) should be $2K - $3K. If you do your own wrenching, it should be less than half that; know that Porsche parts are not cheap. I have owned my 2001 S for four years, and major mechanical items have been highly reliable. However, at 15+ years, auxiliary parts tend to wear out - in my case, ignition switch, headlight switch, turn signal switch, window regulator switches, coolant expansion tank. Most could be DIY. If you can find one, I'd also suggest on with a new top with new control cables/gears - with glass rear window. Doing the "Boxster chop" (search this forum) every time you lower the top does get old.
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