DTT, what this gets to is the fundamental issue in the marketing of “homelessness”: the issue of volition.
Everyone should agree that living on the street and defecating in the street is a pretty suck-ass way of life, for both the person doing it, and the person observing it. The true argument against excessive catering to the “homeless” has never been that they are secretly having lots of fun, or having a better life than us, or driving around in Cadillacs (though there are gangs of “Kosovar war victim” beggars that I’ve being seen shuttled around in vans who I suspect are doing pretty well).
Rather, the argument is over whether the “homeless” are some subsisting and involuntary group who have been deprived of homes, then sanctioned, by the oligarchy (cf. the tone of the OP). Through the late 1980s/early 1990s, the prevailing message was that the “homeless” were just hardworking folk, families mostly, who, doggone it, had had their homes taken away by Reagan. Because he hated them.
And so forth. Read Bernard Goldberg’s Bias. which focuses heavily on this era and this issue, and on the media’s disproportionate attempt to portray sympathetic, “homeless families,” rather than crackheads.
My direct experience with the “homeless” includes limited volunteering at a shelter serving holiday dinners, etc. It was an eye-opener. The clientele fell into two categories: users, and sad sacks, with the former prevailing. There was a fair amount of theft and fighting in the shelters. And . . . I was a bit troubled by the fact that the same guys I saw in the shelter at night, and clustering around the sandwich truck at midnight on the street, were the ones waving signs about not having anything to eat (or, my favorite, “please help with food OR WATER,” as though dying of thirst were a legitimate threat in America) during the day. I saw very few real “families” or people who had just plain lost some home they had earned. Basically most of the people had made a sad succession of multiple volitional life choices (drugs, not working, drugs, family conflict, drugs, abstention from serious work, dropping out, drugs) that led them, not unpredictably, to the streets. The remainder were insane.
Yet there’s been a great effort in America to promote the notion of the virtuous “homeless” person, as opposed to the more-typical drug-addled, work-averse, insane homeless person. America being America and generous, it’s theoretically willing to help any of the above; it’s simply that simplistic mis-diagnoses of the operative problems aren’t helpful. One of my bosses had a wife who ran psych clinics in the 1960s and bemoaned the “liberalizing” deinstitutionalization of maniacs as one of the main causes of “homelessness.” And this is a liberal social worker.
Arguably, the Supreme Court ruling on vagrancy laws and the related restrictions on regulation of vagrant conduct have further exacerbated the problem, to the point where the question might be put differently: Why Are The ‘Homeless’ Failing The US By Not Living Up To The Social Contract Under Which Members Of Society Agree To Order Their Lives So As To Refrain From Sleeping And Urinating On Public Sidewalks Or Bothering Innocent Pedestrians With Their Aggressive Begging?