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I had a very restrictive criteria. I wanted naturally aspirated, convertible, analog and 2+2 seating at the least. This left me with Camaro, Mustang, E92 M3 and 997.2. I went with the 997 basically to get it out of my system, a well sorted E92 was not much cheaper TBH but I may settle on that if running 3 cars wears me out.
I found the 997 and 991's TOTALLY different cars. The 991 is "better", more capable, more comfortable, more everything except a touch lighter but it just looks big and bit too GT in nature vs the "ox-cart" 997.
If I wasn't doing a cab, absolutely hands down for me the clear winner is a GT350, just avoid the 16's. FWIW at your budget in $USD, i'd do a 997 GTS. I will say, I bought a car that had a small front end incident, lopped a SOLID 15K or more off the price. I realise I will need to price accordingly when selling it but the car drives true, the frame is straight and the price point excellent for a 13 yr old car with just 40,000 miles.
Left of field options are the Jaguar XKR-S (hard to find) and Maserati Gran Turismo. I really like the masser but the cab is MONUMENTALLY heavy. IF you can cop 2 seats, you have a LOT of options I did not.
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