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I have 2 911s, both turbos, and neither a 996, but the boxster is more nimble, more immediate, better balanced, and tons of fun on the street. I hate to be cliche, but it really is tossable. While the 911 has the speed and arguably better looks, I just don't see it as an upgrade. A 997S at least ups the power and limit quotient, but its still not any more fun.
Guess you could try it out, doubt you'd lose much money.
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