[philetus]

providing benefits like free meals and free accommodations for a troubled group of people only encourages the expansion of that subculture within a given municipality?

Of course it does.
Lots of addicts can't or won't make it on the street.They like the idea.
Staying drunk and high all the time.
Not having to work, but out of real and imagined fears of being beat up, robbed and killed, they hold down mediocre jobs to house and feed themselves.
Once this program starts, they'll be coming out of the woodwork.

[lelio]

dittos to your post. If this did anything to cure the problem of drunks hanging out in Pioneer Square I would be for it. But you're right, by removing these people it gives another one an opportunity to squat in his spot.
A multi-pronged approach to this might work where they take the drunk off the street for 2 weeks, get them sober and say that if he's caught drunk again he gets a one way ticket to Portland.