Yeah, I did for my last car in 2019. It didn't even have good pictures, including no interior pictures. It was a calculated risk: California car, so likely no rust; it was a car that I know very well (2003 Subaru Legacy wagon); I knew that the interior, electronics, mechanical hold up pretty well; and I would have been happy to pay for a head gasket job and full engine reseal at the selling price ($2,100); I was willing and did put in some time after I bought it to bring all the delayed maintenance up to date and to make the car a long-term keeper. (It could have easily gone the other way with a different buyer, with the car becoming a disposable poopbox.)
I didn't inspect it, or have any locals inspect it, and I didn't negotiate. I had been looking on the sfbay craigslist for a month, and when I saw the ad, I was the first person to call, and I offered full asking price right away. It was a good gamble, and a good car. I wasn't able to travel (to visit my parents) to pick it up until a month later. I put in about $1000 to make it really nice ($250 paintless dent removal for one big dent, fluids, replaced struts/shocks all around even though not really needed, etc.), and then a bit less than another $1K a year later for a shop to put in a new clutch, so about $4K total. That's not counting putting on a set of ultra high performance tires, since that's a wear item.
A car just like mine except auto transmission and low mileage sold for $13K on Bring a Trailer recently and functionally or maintenance-wise isn't going to last any longer (head gaskets already done on mine for one, and longevity will be more determined by the next owner than the car). Pretty good money for a 20-year-old car. So I like to think mine is worth about $10K to me as good transportation and the kind of car that is my all-time favorite (manual trans Gen 2 or 3 Legacy wagons). A 1997 Legacy wagon (essentially the same as my 1996 Legacy wagon except color) sold for $18K recently on BaT, so I guess I'm not the only one that who is really into them.