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I bought a 2000 S that had exactly 100k miles on it about a year ago. It's worked out OK for me so far. The car has needed a new coolant tank, alternator, air flow sensor and some vacuum leak fixes but seems basically sound.
Visit the car when you can perform a cold start. Look to be sure the check engine light is functional - it should light up when the key is turned to the on position before you start the motor. Start the car and listen for bad noises. A little cloud of oil smoke shouldn't necessarily cause you to reject the car. Take it for a long drive and see how it drives and runs. Make sure the top goes up and down OK. If everything works OK and you like the car, think about making an offer. Recognizing it's going to cost you some money for stuff you didn't spot and other things that are going to wear out, consider an offer of $7-8k but it would depend on the subjective feel of the car on the test drive. I paid $12k for mine and I feel I paid too much.
Don't mix your fun car with your transportation car. A 100k+ Boxster will be too troublesome to be your transportation car but it can be a fun car to own and drive if you can get it cheap enough and you like working on projects. Don't spend more money than you can afford to throw away or lose if the car fails catastrophiclly. I kind of wish I'd bought a Miata but I'm 6'3" and I can't quite fit comfortably in one. I think a Miata can give much of the same fun factor as a Boxster but be a lot more practical.
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