The only way I’ve seen this actually work is by buying a car near the very end of its depreciation curve. Like you need to buy a $4k Honda Civic, drive it for a few years and you can sell it for near the same price.

The other way is to buy a limited edition exotic. For example buying a Lamborghini Huracan Performante near the bottom of its depreciation curve, keeping it in pristine condition, putting minimal miles on it, holding it for like 10 years and then you’ll likely be able to make some money on it in the future.

It also works on slightly lower end performance cars. Like if you bought an e46 M3 CSL in the 2000s it can be sold for more than what it cost new. Again it would have to be kept in pristine condition and with minimal miles.