The Sam Vimes “Boots” theory of socioeconomic unfairness, often called simply the boots theory, is an economic theory that people in poverty have to buy cheap and subpar products that need to be replaced repeatedly, proving more expensive in the long run than more expensive items.
The worst used car i bought cost 2k to fix and 2k to buy. It lasted 5 years. I can do anecdotes too. I trust consumer reports actual data over my own experience and yours.
As for insurance, older cars are going to be cheaper because you should be liability only. Which you CANNOT do with a new car loan.
OP asked “When have your done this to yourself”, I gave my example and explained how that happened. Never did I say it applies in all cases, don’t put words in my mouth.
I already included insurance in my calculation by the way.