re: How would you advise a genuinely broke person regarding buying a car?

RE: working poor/poor atittudes/despair.....I know what you mean, and I also know it's a damn shame that mental health care is so stigmatized in part of the USA. Eternal despair is not normal...it is a chemical brain disease. Undiagnosed depression plays such a role in the cycle of poverty; therapy and a short term anti depressant can be a game changer for people whose screwed up life choices derive from deep seated feelings of worthlessness.

If the guy does have a reliable work history & is a steady type who shows up, seems like you could do him a solid by loaning him the money to buy the car & setting up a payment plan. I'd feel compelled to explain why you're doing it---that the financing options open to him are grossly disadvantageous, that your terms are different because you want to help him, and give him a little financial education as lagniappe. Print out the amortization schedule for your loan, go over it with him. Make him realize how much he's paying you in interest, etc. Talk to him about his banking: he may be throwing away $$ each month by using a commercial bank gouging him on fees rather than a credit union (which generally have free checking and savings accounts for members). Tell him why you decided to help him out: have a serious conversation about what makes you trust that he will pay you back, why you want to help him, and how you want him to pass along the favor in any way he can by helping other people.

My husband sold his last car to a college student who was commuting 40+ miles round trip in a terribly unsafe vehicle in need of expensive repairs. Her employer paid the cash up front and is taking money from her check each month...this is a young woman who has a disabled mother (stroke) and an elderly grandmother in her household, trying to finish her degree/teaching certificate. So he knocked a grand off the price out of goodwill...she will graduate soon & the entire household will move from near poverty into the middle class once she has a job. She will be an excellent, emphathetic teacher. I'm sure she'll get a master's degree at some point.

It's nice feeling to be someone else's lucky break or answered prayer. It's easy to look the other way; it takes a little risk to help others. Those of us who have "enough" sometimes forget what it's like to struggle and struggle and struggle.