Is a used convertible mustang, maybe 2019, too pretentious for a guy who's older than 55 but younger than 95? I've never had a convertible or a muscle car.

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Yes, and I'm totally not sure what to do. I would lean more towards a Tacoma I think.

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good choice modern jeeps are hot stinky garbage.

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I keep hearing that, but I also see them everywhere, but that may not mean anything.

I think I will avoid them.

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The company will finance anyone and sell a car to whoever they can convince to buy it...

Look into reliability ratings.