I completely, 100%, understand and sympathize. I've been in a similar situation for a while.
I love my parents. And not all of their current situation is entirely, directly, their fault, but a lot of it is. They recently had a windfall, of sorts, a few months back. I was hoping that, considering the foreclosure threats, the destroyed credit, the really tough situation they've been in, they would finally see to it that the money was put to effective use.
But, no. Instead, they settled a few bills, yes, but several thousands went to my brother, so that he could get a shiny new car that he couldn't afford. My brother works hard, and I love him too. But, he couldn't afford it. He didn't need exactly that one. There were lots of perfectly reliable options for $1,000 or less.
Predictably, he's already behind on paying them back. Then tax time came, and that windfall suddenly added up to a huge payment back to the government -- money they, again, didn't have. Now they're selling one of the vehicles they have a loan on, at a loss, because they can't afford the monthly payments anymore. They'll still have to pay the difference, probably for around a year, and they'll be out of a vehicle in the meantime.
None of this stopped my dad from picking up a really great deal on an antique car, though.
It's maddening. It's definitely starting to put a rift in our relationship. I've tried helping, a lot. I made their car payments for a while (and in return got to drive it while mine was broken down, yet again). I've been paying their cell phone bills for around a year now, at least.
Meanwhile, I've bootstrapped my own business, with no savings. I work on my truck constantly. My girlfriend and I live in a small place; we get by, but it's been very difficult sometimes. Gradually though, we're getting ahead, and without much in the way of help. Mostly, we work at it constantly, and try to make smart decisions money-wise.
But my parents, and now my brother, do seem to feel very entitled. They would probably object to that, but if you listen to them, you hear things like, "I've worked hard all my life, I deserve this." Well, no. They worked hard all their life, but they squandered everything they ever made. Now their time has run out and they don't have any options left -- but still, it's someone else's fault that they're being forced to give up all this stuff.
I think it's the Boomer Generation Problem: they were told, "work hard, and you can have whatever you want", and so many people believed it. It was supposed to encourage them to do something meaningful with themselves, but instead it encouraged them to compete with eachother over ever more extravagant displays of wealth -- all of which kept actually making them poorer.
It's very sad, and I fear that not enough of my generation has really begun to realize this yet.