Great post, thanks for the ideas. I daily drove an NB Miata for years and it was okay, but I always felt they were a little overrated. I haven't looked too much into the newer Mustangs, but a 5.0 Coyote version is definitely doable in that price range, as are some Challenger R/T and an SRT8 or two.
There's a mint 2001 Z06 with 13K miles on it for $29K near me. Now that is tempting.
Yeah, a GT would be a little more nimble, but the Chargers are a great cruiser. I had never had a Ford product before I bought my '16 GT convertible, I wanted quick, sporty, backseats, and I did cross shop an M3 cab (we had 3 other BMWs)
Then I wanted a little upgrade, cross shopped an M again, would up with my current '19 GT convertible, this and the '16 were both Perf Packages, but the '19 was available with an auto, it's the A10 (backed by a TORSEN 3.55 rear), it's got magnetic suspension, all the goodies, really a ton of fun (the few times I drive it, I've put like 3000 miles on it in about a year). Running custom 20" wheels, tune, a few other odds and ends
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A C5 Z06 is an interesting option, they pretty capable, I had one nicely setup (photo below, custom rear/hood, wheels, brakes, suspension, heads/cam), I got mine through a factory delivery program, it was a pretty neat experience. The LS6 is solid stock, and a H/C away from 500HP - the interior is a touch dated, mostly the center stack, but they're pretty solid. The seats are mediocre, especially for the "track model", I put in these really killer custom seats based on Porsche GT3 frames, custom leather with exterior matching rear shells.
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Tracked it several, times too, including when it was new with less than 1500 miles on it, at Roebling, bone stock.