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Your price range will reach a Boxster S with a glass rear window easily. I got my o3S with 21k miles on it 2 years ago for 21K dollars. There are interior room differences between the 986 and 987 models, so test drive both for a comfort check if you are a big guy. I can't drive a 987 because my knee hit's the center console (I'm tall). I had to stick with a 986 which has a removable console.
You can't drive either a base or an S anywhere near their limits on the street (if you do you should be locked up) but that said, I do like the extra oomph with the S.
If I was doing it again, I would put aside several thousand of my purchase money (or budget for the near future) to spend on those things you will find you want to do -good tires, upgrades or IMSB perhaps.
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