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The Boxster has the benefit of being old enough that in most cases it doesn't come off as showing off or something abrasive. It's like a guy at the gas station with an old mg. The 996 sadly seems like you wanted to buy an exotic, (you basically did they're such capable cars, as is the Boxster) but with the 996 you're open to way more criticism. I would fear worse public opinion in a 996 then in a Boxster. Also, if mileage was even (911s always have less mileage, Idk why,) I already think Boxster S cars would sell for the same as 98 and 99 automatic 996 cabs.
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