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I'm not a big expert on the subject, but I think in terms of feel you probably won't be getting a better car than the Box, unless you get a track day car or something.
Why not get a newer Boxster S? You can get 987 S (maybe a used one with 10k on the clock?) and it would be reasonably cheaper than 40 grand.
If I was in the market, I'd be looking for an SLK or Audi TT. Since you do switch cars so often, why not mix it up a bit and try luxury-sport?
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