Heh... one must face the facts, cars are expen$ive.
You can buy a new or almost new car, and make payments, and if under warranty, it shouldn't give any trouble. Sadly, I've known people who had new cars who have had troubles with them, and dealing with the dealership (pardon teh pun, not intended) it was one long series of headaches.
Me, I'm usually the last owner of a car. Down to the dregs. But the cars I've had were pretty good for the price.
What it boils down to is 2 things:
a) what you can afford to buy
b) what you like so much you don't mind putting money into it
The decision hinges on whether it's worth putting more money into it, or turning around and buying another car, and possibly dealing with its problems, if any. Usually the biggest factor is rust. Rusted cars ultimately aren't worth fixing up.
The other thing is, how you treat it. If you don't tear around town like most people, then it will last longer. If you change the oil and maintain it regularly, it will last longer. If you live in a place that does not have harsh weather conditions, like salted roads in winter, etc. then it will last longer. If you don't have to commute every day to work it will last longer. In other words, in a perfect world, it will last longer.
The car manufacturers don't want their cars to last too long, or they will go out of business. Look what happened to the Checker cars. Sure, they were bought up by the cab companies, but you probably could put half a million miles on them, and so after a while, no one is going to need to buy another. You could buy a used Greyhound bus, those last a long time... many of those literally have a million miles on them.
To be honest, if I may ramble on, the newer cars to me seem too flimsy and don't hold up long after they're paid off. Older cars may be clunky and not good looking, but they are better built. Having driven a few rental cars over the years, the only one I liked was the Nissan Altima. The Buick Century was atrocious, and the 2000 something Chevy Astro van, ehh, wasn't bad. Toyota pickup, gah, no power, and a pathetic little horn. The Subaru Outback is nice, but it doesn't last. The engine plppts out at about 130K miles.
Probably not very helpful commentary, I don't exactly fit the status quo, LOL!