It is tough to pick a path to follow and stick to it and always believe you're doing the right thing for yourself and people who depend on you. Perhaps that's why there is a tendency on this board to "jump on" stories about folks who don't participate in a life of frugal living or who don't maximize earned dollars, or both, in order to gain FIRE status ASAP. Of course, this forum is about FIRE, so I guess the tone should be expected. It wasn't an easy decision. I tried to make sure I was following the logical path and not the emotional. In the past, my friend has given several of us some flack for living conventional lives (jobs, families, houses; the whole catastrophe) while he was much more unconventional. I didn't want my decision to be based on a "get even" point of view. I think I'm doing the right thing. He needs to come to grips with being older and having eaten his dessert first which will probably involve moving to a no-car area and living in some kind of subsidized or shared housing. Helping him get a car now might enable him to stay put for a while but, more likely, something else will come up that can't be handled with a mid-teens income and the decision would have to be made again.