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I own a 993TT, just recently sold a 997TT, and have my 99 boxster 3.2 and to be frank, the boxster is just such a fun car to drive. Its a perfect blend of power, handling, useability, etc. I don't find the car to be attractive looks wise, especially compared to a 993, but its truly a toss up when it comes to what keys to grab.
a 986 with a beefed up 3.4/3.6 is an absolute blast at the track and you'll catch more expensive hardware no problem.
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