I have not had a car with payments, so I've not sold it-but I have lots of experience with older cars
Currently in our household (3 licensed drivers, dh , me, son) we have a 1995 Gmc Jimmy, a 1997 Chevy Cavailer, a 1998 Chevy Astro, and our 'new' truck we just got, a 2001 Dodge Ram. Our first new millenium car, lol. Dh also has a project car, 1978 Trans Am (this is not a daily driver).
Here, we pay property tax on registered vehicles. The property tax on the 4 registered cars,
together, is less than I'd pay on
one new vehicle like an SUV or van! Insurance, even for my teen, is low too. We only carry collision on the 'new' truck, the rest we carry the legal requirement. So we save there too.
If you have 2 cars in the household, if one breaks down, you can share during repair, so I don't worry too much about breakdowns. Once, when we just had the Jimmy and the van, the van was in the shop (for something dh couldn't do at home) and I rented a car for a few days. It wasn't a lot of money (it was a toyota yaris, which felt like driving a lawnmower
). It was way cheaper than even just one car payment. We do have AAA, and have used the tow service-we consider it a good thing to have with our older cars.
Dh does a lot of work on our cars himself, so that helps. If you/dh aren't car handy, often a local high school with an auto shop will work on a vehicle for learning, for just the cost of parts. We've done that.
I think a lot of people are afraid of older cars, but my experience has been, that they tend to run well for longer than people think. I live in the NE and haven't had lots of rust, like cars used to do years ago. You could always try selling your car and getting a paid-for one, and if after a year you just don't like it-sell it again and buy a new one.
I will admit, while I am happy with my old, unfancy cars-I did
love the Chevy Traverse I saw outside Test Track last year!!!
Maybe in a few years, I'll find a used one for cash, lol.