I have a family member like this. He makes a good income, has very little in the way of obligations (renter in a one-bedroom apartment), but spends so stupidly I want to smack him.
Right out of school, when he first got a job, he bought a Jeep (a TJ, at the time). 10 years later, he still has it, but he's put THOUSANDS of dollars into it getting it jacked up, getting fancy tires, installing neoprene seats, getting fancy covers, towing systems/winches, etc. It was his only car and he found the gas really expensive.....because it's a beast.
I should add that he very, VERY rarely goes off-road with it, and lives in a large city.
So what does he do? Not sell it and use the proceeds to buy a reliable, well-priced used car.
Nope. He stores it in my garage.....and bought a Volkswagon Golf TDI. New, of course. Fully loaded, of course. I think it was something like $38k (Canadian) after all the options and tax. He buys this because it's "good on gas" and has now saddled himself with a car payment for YEARS on a car that is only marginally better on gas than a car he could have paid cash for, had he been willing to sell the stupid jeep.
He recently told me that he won't be taking the Jeep out this summer (again, too expensive) and it will just live in my garage.
It just drives me crazy....seriously, he probably could have sold the Jeep for 13-14 grand, bought a great used car and had no payments, and no stupid Jeep sitting in my garage. I let him leave it there because I have lots of space (we have one small car and the garage easily holds eight....thank the previous owner of my home for building it, because I never would have). But because he'll "never get back the money he put into the Jeep" he leaves it sitting idle (and losing value), and because it's "good on gas," he is spending a fortune paying for a brand new car.