Years ago, at the end of a disability assessment, a psychiatrist told me that he believes that ultimately, people do what they want to do. That is, if someone wants to work, they work. If they don't, they don't. Somehow, in spite of that little gem, my case was approved, anyhow.
More recently, as I've read all sorts of articles about helping the homeless, I've seen a common response about how some homeless people want to be homeless. As if, therefore, there's not much point in trying to help any of them, or something nonsensical like that.
That's not nonsense because it's untrue, however. There's actually some truth to that. Sometimes homelessness is a choice, in the sense that it seems better than any of the alternatives society provides. Often, because those alternatives are pretty damn awful, too - or because they are beyond the scope of what someone believes to be realistic or manageable for themselves. There are often mental health issues involved. People do not pursue options which are all too likely to be painful and unrewarding. Those aren't really options, in any reasonable sense.
If living in a homeless shelter is actually worse than being homeless, that isn't really much of an option. To get a soulcrushing awful job for slave wages, only to remain in poverty anyhow, that's not really much of a choice. To look at these choices people make as some sort of bottom line is just a way of shrugging off guilt. It's pretending that someone's misfortune is their own choice, just because to some relatively inconsequential degree, it is.
So, that psychiatrist was right, in a way. People do not make their choices in a vacuum, though. They generally make the best choices they can, given what they feel capable of, how rewarding those choices are likely to be, how painful they might be, how likely it might be to go horribly wrong, putting them in an even worse situation, etc, etc.
Even drug addiction has been shown to be a rational decision, in a sense. Put rats in a barren cage, with nothing to do except drugs, and they self-medicate themselves to death. Put them in a cage where they have all sorts of engaging alternatives, and suddenly they're not addicts anymore.  
We don't always have the best judgement, to say the least, but nobody intentionally makes bad choices. People do the best they can, given their choices in life, as they understand them. Dealing with parameters other people are often unaware of, or completely unfamiliar with.
Passing judgement on people for failing to adequately navigate a difficult situation isn't solving anything, other than how to suppress sympathy for our fellow human beings.
Not the most noble of goals, really.