I'm interested in modifying the system which allows for such outcomes, not managing the outcomes themselves. Please take a systems-level approach that seeks root-cause adjustment and not simply an amelioration of symptoms.
I count myself as progressive but am almost disgusted by how many progressives try to muddy the water here because they don't like to face the fact that they have to give something up to make their neighbourhood more accessible to those who are well-off people.
Anyone who doesn't take housing policy seriously on the issue of homelessness is either naive, or doesn't actually care about the issue and instead is trying to use it to push some other agenda.
Where will this person find a job? Where will this person get help organizing their lives? How will this person transport themselves? Where will this person get help for any significant issues in their lives (e.g. substance abuse, mental disorder, etc)?
This is where your "system-level approach" breaks down - you can't bring the support infrastructure for this to a small Vermony ski town and also to all the other small towns in America. This is, as your first post says, poor resource allocation.
Zoom out a bit and observe the broader systems which conspired to guide the invisible hand to allocate a largely unproductive property in Vermont to exist in the first place. I'll be very clear - I'm not advocating for unhoused people from New York to inhabit this property. If that's how you've decided to read it I implore you to go back and begin steel-manning instead.
Even high-functioning and privileged individuals seldom have their shit together 98% of the time. I can't go 5 days without doing something chillingly stupid.
It is frankly astounding that we achieve better than 98% on any homelessness metric. A long forgotten ancestral memory says: there but for the grace of God go I.
Root cause: humans stink individually but we are robust in aggregate.