I know someone like that. It's not pretty.
He's is turning 71 in couple month. Had variety of jobs through out life. Went through two divorces. The second one was finalized earlier this year. Was homeless for few years in early 2000's and lived in his car.
Now at 70, he lives on SS. I think that is about $1800/mo. Does a bunch of odd jobs to pick up extra cash; looks after an older couple (couple is in mid to late 70s, but in much worse health than he is), does handyman type jobs, cleans snow in the winter (he has a showell for his truck, so he does long driveways, some small private roads, and some business fronts).
He's covered by VA medical, but I have no idea what that entails. I know he was in VA hospital about 2 years ago, and I know he has no cash/savings to pay for medical care, so I assume that was covered by his VA medical benefits.
Now that his second divorce is finally resolved, he got about $14K out of his ex's 401K and a time share in Vegas. The time share is for a New Year week, supposed to be very fancy/expensive and supposed to give him ability to rent or trade it for other locations. But, Las Vegas is on the side of the country and he's not likely to be there, or anywhere for that matter in foreseeable future. No other savings that I know of.
All in all, he manages. It helps that he's in a relatively good health and has a very positive attitude and outlook on life. He rents a small apartment from the couple he takes care of. It's a tiny 1 bedroom not in the best of shape, but it has all amenities, basic as they are. The money he earns from the couple for driving them around and such is what he uses to pay them back in rent.
Before that he lived in a really crappy 1-room basement apartment for over a year. I was happy when he finally moved from there as it was truly depressing - no windows, bed was taking basically all of the living space, the owner was constantly in his business, etc..
He has no plans on what to do with timeshare, so for now he's planning to just pay annual maintenance fee on it. I mentioned selling it, but he won't hear of it.
At this point, it looks like as long as he can manage on SS he should be fine on day to day basis. He does enjoy life as much as he can. Always in a good mood. Always smiling. Dating a lot. And generally living.
I have no idea what would happen if something serious medically comes up or if he needs long term care. I don't know if he would be covered through VA or not.
He has a two grown children, daughter and son. As far as I know he hasn't see his son in years and he sees his daughter about once per year. There is absolutely no help that he gets from them. Not sure if he has any other relatives, but I know he doesn't get any help from anybody.