The social and political environment for the unhoused, as well as the substance abuse environment, has shifted during those 20 years. Many homeless people today are exactly where they want to be. They don't want to come up with rent every month, please a boss every day. They want to do street drugs without a care in the world. Sometimes it's an easier way to avoid confronting mental issues.

20 years ago if you asked an unhoused person to leave a Starbucks, the fear of police, the general shame, etc. soft social pressure might have worked. Today's street residents might see the antagonism as entertainment, their position in the world as entitled, and sleeping in the police lockup as a clever free hotel hack. It's the same sense of entitlement that has them break someone's car window for something they can sell for $10 or walk out of a store with an arm full of merchandise.

In a way, the breach of social contract has become an entertainment aspect, if not a Robinhood-esque anti-society self-justification. The consequences of "being a constructive member of society" are too high for many, and the consequences of street life are ones you can mentally harden yourself against.