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I have used Turo a couple times (admittedly, a few years ago), and ultimately I don't really think that it's worth it. The main pain point is the hassle that you get to skip if you're renting from a company. The coordination at pick up and drop off is not seamless the way you can grab keys from the counter and then drop off the car. I've never had to deal with insurance, but that makes me a little wary as well - nobody at the Avis will really care about a door ding, whereas a Turo rental person might be more particular. My company has a rental rate that includes all of the insurance so even if something were to happen and the check-in person were to notice, it wouldn't be a big deal.
My $0.02: you're going to the Keys with your wife - I'd skip the nicer car in favor of an easier rental process for a car you don't have to care about.
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