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> (1) People are comfortable on the streets, they enjoy the freedom, or they are at least accustomed to it, and paying rent/bills seems anathema to them.

This has to be the most peak late stage capitalism shit I've ever read here. It's not a terrible idea to keep a few things to oneself I guess...

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Have you ever actually studied hobo culture or anything? I mean there have been whole classes of people, let's include the Romani, Bedouins, and Travellers, who love itinerant lifestyles and are, for all intents and purposes, "homeless people" who find a means of supporting themselves that doesn't involve sticking around in one place. They are all, of course, universally reviled by capitalists and communists alike, but whatever.

There is no population that actively rejects any form of housing (cardboard boxes excluded) and if there is, they definitely aren't moving to large urban areas en masse.

And even if it's the case that they were formerly sheltered but 'decided' to be homeless again, it's probably the shelter provider that didn't do a great job at accommodating them.

In any case, cultural opposition to housing is a pretty weak argument to make in order to express despair where your valuable taxpayer money goes to.

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