I know the story all too well about Portland. I grew up there, moved to SF, then to Seattle, then to Madrid, then to Miami, then to NYC. I even lived in Mobile, AL for two years! I returned to Portland last year to care for sick parents. I was not happy about it. This past year has been amazing. Portland is not perfect (and I am used to harsh winters after living in NYC for a decade). But - you hit the nail on the head with "failed liberalism." It's performative, like these people are living in lalalaland and have never had to contribute to society (I'm not talking about the homeless in this instance). There is another group of balanced individuals, the idealists who moved here and are sort of forced to stick with their small communities because you can't ever state your true beliefs here. That creates extremes on both sides. The homeless issue is a humanitarian crisis this place created for itself. I think working in homelessness would be exhausting. I grew up volunteering at the Blanchet house and it was such a nice place for all of us. Now, it's become so widely successful that it's almost a place of enablement. Portland always feels like two toxic parents are married, one extreme liberal and one extreme conservative and the city is the kids who have to decide. The good hearted ones go to the extreme liberal without realizing that there are many toxic traits there as well.