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Originally Posted by Flat Spin
Therefore, I am starting at the beginning. What car should I look for? Which one should I stay away from?
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My preference is the S over a base, however, as mentioned, the base tends to be more fuel savvy. There has been difference in early 986 up to 2005 which began the 987 series. '03's were updated with glass rear windows including some body changes. 97-99 were fitted with 2.5 L, '00-'04 introduced the 2.7 base and 3.2 S. The most important thing is the due diligence required before buying a Boxster.
Boxster are reliable cars, parts tend to wear out as with any car. The major checks I have performed is inspection of the rear main seal (RMS), coolant expansion tank, water pump, O2 sensors, mass air flow (MAF) sensor, suspension, brakes, clutch, and of course any check engine history. You need keys (all three, codes included even better!) manual, wind stop including roll bar covers, wind stop carry case, jack/tow tools (all of them), and cd changer cartridge (if equipped). More is always better in the transaction, including the service history, get as much information as possible!
I purchased my '01 S for 22K, people can't believe it! It still looks like the original 52+K sticker price, however, I have invested close to 2K in repairs in a little under 1,500 miles. So, plan on putting some money in the car after purchase. My experience is that the cost of ownership is high in the beginning, leveling out after 6 months or so.