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I have owned both, a 1999 boxster currently, and a 2002 Cooper S a few years ago. Also working at a car dealership I have opportunities to drive the newer Coopers.
The newer Coopers ride a lot better than the first generation. They do not handle very well compared to the first generation though. The superchargers do not seem to hold up too well, they lose boost as they get older. They are about equal on hard to work on, and about equal on cost of parts.
With that said, they are two completely different cars. I like both(first generation only of the Cooper). If I had to pick between them, I am not sure which one would win. Only you can decide.
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