This is the significant distinction between providing crappy shelter and providing a home. A lot of shelter spaces come with a lot of strings, and the first step to fixing the issues is to accept that you need to cut many or most of the strings - if a significant proportion of homeless prefer homelessness to the help you're offering, perhaps the "help" isn't all that helpful.
If you want to get people off the street, you need to provide a similar level of freedom in the housing you provide as what it replaces.
> (3) People are naturally generous/irresponsible with belongings and income that they will spontaneously share the windfall with everyone they know. So your shelter for one man will end up being a flophouse for a rotating cast of shady types
Is it worse having them in a house than on the streets? And how much of a problem is this going to be when everyone involved have their own shelter? It's only a windfall if you provide it to a few rather than everyone who needs housing.