A lot of the homeless have severe mental issues. We are simply not equipped to deal with such people.
Several years ago, when I was managing a thrift store for a homeless shelter, I encountered a woman who drove up in a very confused state. She was convinced that she needed to drive north to Flagstaff and she did not appear to have sufficient funds for gas. I got the appropriate social services representative on the phone and it took three of us to convince her that the trip was not a good idea.
Right up front, a major issue was one of trust. It was a very hard conversation.
I was on Reddit (R-Bay Area) today on this subject and its interesting, a lot of them are against this, and reddit usually skews to the left wing. One person in particular who was upvoted argued that what we are doing is not working when dealing with the homeless, the ones who have mental issues need to be put in mental facilities that need to be reopened and the ones who are on drugs, alcohol, need to be put in a forced conservatorship that will put them into locked area’s and can leave when they are better. Not sure how I feel about all that but we are doing sure as heck is not working especially subsidizing them.