Alternate take: he could be a really shrewd buyer and good at selling privately.

Probably not, but it’s possible. I knew a guy whose hobby was entirely cars. Shopping for them, going through financing details, and sometimes buying them. He’d bolt on some mods and seemed to have a knack for finding buyers. He’d sometimes sell for more than the total amount he’d put into the vehicle.

He had almost no real understanding of cars. At most, he could do an oil change and slap on a K&N filter. But goddamn did that guy ever understand how to manipulate financing to his advantage.