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Upkeep isn't cheap on Boxsters or any other Porsches. Generally speaking, buy a Boxster in the best possible condition with your desired options from the start.
I've got a '99 Boxster that I bought for $12,500 with 25k miles five years ago. I'm now up to 81k miles and have spent at least $6000 over that time on the car. Many parts aged and needed replacement regardless of the low mileage of my Boxster when purchased. I dare say that out of the four owners it has had, I'm its first enthusiast.
If I were to sell my Boxster now (which I have toyed with from time to time), I would be lucky to get what I spent on it 5-years ago (ignoring all the repairs and improvement costs made a long the way).
If you want to join the Boxstering crowd, great! These cars are so much fun. Just do yourself the favor of doing your homework first. Try to find one with the IMS bearing already retrofitted at least. Replacement of the water pump, AOS, coolant reservoirs, window regulators, motor mounts, ignition switch, and suspension (etc.) are all instabilities too, so look for one with as much of those fixes on the books as possible too.
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