Being poor sucks.
Yes, that's right: being poor. I'm talking about the constant stresses placed upon a person that is working a minimum wage job, barely able to afford their rent. Constant stress about money.
Now imagine for a minute I could tell you that stress is a choice. The alternative, the very scary "homelessness", "on the streets" --- is it really much worse? Could it actually be less stressful?
I think what happens is some of these people become homeless and realize that it isn't all that bad. For a subset of the population who can already get by on not a lot, not having a home (and the stress that comes with it) must be welcome. They become homeless and realize "I can do this, this could be my life. Let's live in a tent."
And there you go, someone who has decided to become "chronically" homeless.
I'll have to say there is something to be said about releasing all the conventional trappings of modern society: you no longer have to worry about bills, responsibility. You get to be outdoors. Sure, there are other problems, like where to find food and keep clean, and avoiding the police, but for some that is better than competing in the rat race of life, at what is the very hardest and poorest levels of society.