Unfortunately, from family experience, some people just can't or won't learn. When/If they start to get their heads above water, something happens to cause everything to fall apart again. Often, it's interactions with other people (a bad boyfriend; believing a story that a better job is available in another city; etc.). Sometimes, it's just bad luck (an inopportune injury or illness; a car that breaks down too often; etc.). Sometimes it's laziness or fear of making hard choices. And some people just never have enough income to live the life they think they need to live and there's no convincing them otherwise.
Most people will eventually get the hint that they need to take responsibility for their lives and get their acts together. But some won't. My mother was often in the "can't get their act together" group. The problem is - what can or should you do about such people? And how do you tell the difference between the groups? I don't know.
Starting young and impressing on kids that life is a series of choices that will impact everything they do or want to do is important. But it doesn't always work, in spite of your best efforts. That's when things really get hard, as you've found (and I've experienced). :-(
Sometimes people need to be rescued. Sometimes they need to claw their own way up the cliff. It's very hard to know the difference.
Best of luck, everyone.
Cheers,
Scott.