My mom's best friend of 30+ years never saved any money, plus refused to take/keep stable employment that was well-paying--an "ain't gonna work for the Man" approach that sure as hell hasn't worked out so hot for this particular woman.
She has been teetering on the edge of homelessness for several years now. Currently, she's 68, collecting about $750/mo in SS, unemployed,and sharing a rented travel trailer in an RV park, with no car and limited access to public transit She's got a difficult personality, so while she was eligible for some decent shared, subsidized women's senior housing in a good location (near shopping, services, potential jobs and bus routes), she didn't get in after pissing the wrong people off. Her utter inability to "go along to get along" is part of her undoing.
I'm pretty sure she will end up truly homeless within the next year or so. Her personality plays a huge role in that, but she's also in declining health, and is pretty much unemployable. But even if she did magically grow some humility and the ability to just do as she's asked without a fight, and exercise some impulse control, she'd still be stuck working at low-wage jobs until she's either dead or in a state facility.
Then there's the 60-something Metro driver I see on occasion who lives in a rooming house in my neighborhood because it's so cheap. But he says he'll have to leave the Seattle area and retire elsewhere--maybe even Belize--because he can't afford to stay in Seattle. And I'm thinking, "Dude--you drive for Metro. You've been driving for Metro for at least 20 years, maybe 30. You guys get paid fairly well, have access to things like 401ks and pension plans that self-employed me doesn't--where the fuck did all your money go, bro? Booze? Indian casinos? Hookers? Seriously."