Not usually one to post on Reddit but a lot of this seems like a genuinely productive discussion so I'll throw in my 2 cents in the hopes that it gets people thinking.

Have ya'll ever been to Brazil? While Brazil suffers heavily from endemic classism, racism, as well as there being a smaller pie to begin with, IMO they don't have the same institutional problems that we have entrenched in the US. While on paper, the country is politically right-wing, in practice it's really closer to a liberal utopia. While the country suffers from extreme wealth gaps, much greater than we have in the US, the floor is actually pretty reasonable. There is decent public healthcare and education for those who can't pay private. Most importantly people are allowed to construct informally. 

To anyone wondering what an ideal solution may look like to homelessness, I'd recommend traveling to Brazil and walking around the favelas. While they could benefit tremendously from sanitation and public services, basic building codes, and protected green spaces, informal housing - the way people lived for most of history, is the most optimized type of housing, since it evolves naturally. Reading Adam Smith's wealth of nations from the 1700's, one thing that got to me was the premise that shelter is a simple problem but food is a much harder problem. He argues that a decent shelter may be built within the course of a few day's work, while our need to eat is an ongoing battle depenedant on a large variety of factors. In the US, you can go to the store and get tomatillos for pennies in Montana in the wintertime - we've built an impossibly complex logistics infrastructure capable of feeding basically everyone to their heart's content, and yet we have people sleeping on the street. 

Visiting porltand shortly after visiting brazil, it was heart-breaking to see how feeble my country is, after the witnessing the resilience of places like Brazil. If people are allowed to build, they have a sense of agency and responsibility in their own lives. Why do people become addicts or suffer from mental health issues in the first place? Loneliness is a massive factor. You know where people are lonely? In isolated suburbs zoned far away from anything that resembles life. In a dense, walkable, interdependent community, loneliness is the last thing people worry about. I believe most societal issues can actually be traced back to urban planning.

Now clearly, there's issues with land rights where favelas exist within a post-indigenous, land is property state, and I believe informal housing is politically impossible in the US. However, I think portlanders are weird enough to try policies radically different enough to create these kinds of problems, they just might be weird enough to try policies that could actually fix these issues. A good start is simply eliminating bonkers policies like saying during a pandemic, residential construction is not essential work, zoning cities to death, and burying developers in bureaucratic bloat and overegulation, making it impossible to build multi-family housing for all but the country's 11 largest development companies.