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I recently bought a '99 and I couldn't be happier. Most fun car I've ever owned, and I, too, have had Corvettes before ('68, '84, '92, '09). Where the 'vettes are all raw flaming power ("America, f*ck yeah!"), the Boxster is sophisticated and sensual. Compared to the 'vette, the Boxster leaps around corners lightly and effortlessly.
My 21-year old Boxster with 50K miles is still in rock solid shape. Tight. No squeaks or rattles. Feels like an extension of my body. And it has been very reliable so far.
As far as handling, it's superior to any 'vette I've owned. However, I'd prefer a little more under-steer. Steering is very neutral in corners. I like to feel a little more resistance. But that's just preference. It handles like a dream.
Also, I've been surprised how many comments my ol' '99 Boxster gets! People really love how it looks (and so do I).
I'd buy one again.
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