. . . Kindness, cat and mouse raiding and moving, attempts to find "housing" (give such housing to people on the edge, but who've legitimtely fought successfully to avoid homelessness, with priority for families with young children), is just not working.  At the very least, the optics simply do not support pursuing these things further.  The guy with the bike, furniture and beer brand decor is just a bit too much.  He can obviously move furniture, or rehab bikes.  And, unless he's sitting in a tent on land he owns, or has permission from the landowner to be on, he's trespassing.
And, if the State is giving permission for the guy to be on the land (which it tacitly is), then what's to stop any or all of us from setting up housing.  Mine would be nicer, and more secure.  Probably bring along a generator or two.  Have refrigeration, TV, etc.  Do a year on the streets and let my other assets generate income.