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Notes -
The car I actually had in mind was a Civic Type-R, though there are a lot of cars you could sub in here, the idea being that these are normal cars designed for normal driving that have just been modified a bit for performance. The problem with the S550 is that for the price you quoted you're only getting a V6, which is a mid-life crisis car for a woman. You can get an S197 for that price but it's probably been in at least one wreck. I don't know how much a C6 goes for these days but if OP went that route he should spend the rest of the money on veneers and hair dye and head down to the local suburban townie bar where he can hit on hairdressers who bitch about how their ex-boyfriends are always late with child support.
300HP is arguably more than enough for this use case; the S550 doesn't look as nice in my opinion, but is still the better car over the 197 (especially the 197s with the 4.0, which really is just a Miata with 4 seats and more room). I guess the Camaro counts too but the interior isn't as nice.
And then the Corvette, which is... also just a Miata in terms of practicality, but one on which the LS swap was done from the factory.
Not that both don't have the same kind of stigma, since the Ford has My Little Boomer on the front and the Corvette defines the archetype. That being said, though...
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