Do you work with the homeless? I have a family memory who does, busing to and from 6th & Howard every day. Do you know what's actually going on out there? A neighbor's daughters lives on the streets, willingly. Every affordance is continually made available to her, but she's incapable of pulling herself away and there are no longer any forms of legal coercion available. Shooting up on the streets everyday and literally, physically wasting away is not only acceptable to the community but justified. Real, immediate human suffering is excused in the name of abstract, perverted principles and self-serving indignation.
The city spends more than $40,000/yr per homeless person, a sum that has been rapidly increasing for a decade. No city spends more money on the homeless than SF. The reality is that if you're actually homeless and living on the streets you can and will get permanent housing in a matter of months if not weeks, provided you're willing to make an effort at rehab.
The intransigence of street homelessness is at this point a deeply structural issue--medically, legally, politically. It has almost nothing to do with money. The affordability crisis is largely borne by those struggling to get by, sharing accommodations or living in vehicles--nominally functional citizens who aren't shooting up and defecating in the streets. Because providing services to the street homeless and housed addicts is priority #1, #2, and #3 at City Hall, everybody else is effectively locked out of housing assistance. And while more money could help these people (and hopefully will), you'd have to actively direct it away from existing street homeless programs. Without reforms that permit and demand the community to coerce treatment for mental illness and drug addiction, no amount of additional funds for street homelessness is going to substantially change things.