I agree, most prefer the lifestyle because A) life is hard and B) they adapt and/or give-up.
There are 25,000 homeless in my city. I don't know exact numbers but a lot come here to pursue their dreams and some to escape a bad situation back home.
But it is so expensive here. Housing is difficult. Deception is everywhere, in terms of convincing people they have a chance at a career. But more often, they fall into drugs and prostitution, and running the streets -- because it is fun and easy, at first.
So an 18 year old kid who wants to be a singer, can run around meeting interesting people, act like he/she is achieving their dream but really is just partying. Then their irresponsible ways get them on the street.
And a once bright kid becomes diminished by drugs, and stress, and the struggle and emotional pain and torture that living on the streets causes. They then look "mentally ill" but most, in my experience, are merely exhausted and are irresponsible.
I have young friends who are homeless, and I'd start my day drinking coffee with them at Starbucks and then later eating breakfast at my building (a 5-star hotel) with people who could afford to feed a million people for a year.
And my rich friends, a lot are on drugs, and some do insane illegal things, and are generally way worse for society than my homeless friends. And I could often trust my homeless friends more than my rich ones.
At the time, I lived in an $8 million condo for free. And through a conflict of over our philosophies on pandering and prostitution, I moved out abruptly, and was nearly homeless myself. I then got to experience first hand the atrocious public transportation services, the difficulty in renting an apartment and how the City just doesn't care about working class people or the homeless.
The City is inept and just not thinking about solving the problems in a valid way. Instead, they take away electrical outlets in most areas which just punishes tourists, commuters, regular working people etc.
And great institutions, like the pubic libraries, which Carnegie saw as a way to lift up all of society, become refugees for the homeless.
Of course, the majority of homeless people are too far gone. Most are lazy, selfish, destructive and just terrible people.
Were they like that before or did they learn to be that way? Maybe if schools taught kids critical thinking skills and stoicism and how to separate themselves from the emotions, then we'd have a stronger society that knew how to deal with adversity better.
A lot of people, rich poor, smart or uneducated, are slightly fragile and weak. Life is hard, for us all, and society doesn't teach us how to live life very well.