I guess I'll chime in here. I normally don't talk about homelessness as I had a distant cousin (grandpa's sister's son) that loved to be homeless. So my opinion will be quite negative/biased.

But yes you are right about SF. This cousin of mine would regularly leave his family and travel around the US hitchhiking for one or two years at a time. He spent most of his time in Cali, not sure which city. He said it was great to go there for the winter as at that time senior citizens (he was not a senior but he would pass based on looks) could get free public transit tickets. So after a long day of panhandling or drinking, he'd get on a nice warm bus for a night and sleep.

He seemed to be part of some kind of "homeless elite". There was nothing wrong with him physically or mentally (other than severe stubbornness) and it was the same with this group of friends he would regularly meet up with. They would all be in Cali for the winter. They'd bum money on the street pulling in $100+ a day and spend it on alcohol where him and his buddies would sit around in an alley socializing over how everyone is stupid. After winter they'd all disperse to Chicago or the east cost (not sure about NY). He'd randomly run into his buddies throughout out the Spring and Summer months in other cities as well.

He talked favorably of Cali and the east cost. There were some overpasses in Texas on I10 and I35 that he mentioned were also where the cool guys hung out at, can't remember were exactly. But he didn't really like Texas much. In Austin he would be quickly arrested for "vagrancy". This would happen in San Antonio too, but before the cops would haul him off he would call my grandparents about 20 miles away to come pick him up.

I stayed off and on at my grandparent's house while going to college for 4 years. I had the pleasure of rooming with him many times. When he would show up, my grandma would wash his bag of cloths, but it would stain the inside of the washer black, so she'd have to wash 'em a few more times and then eventually wash the washer by hand. His first shower hot off the streets was also a doozy too. The walls would be caked with globs of this white jelly type stuff. I can only assume it was from massive amounts of built up dead skin that washed off. But it would glob up in the drain, and along with his long uncut hair, clog everything up. It was totally gag-tastic cleaning it out. The last few times he came around, I was too annoyed to deal with him again so I convinced the pastor at a local small church to let me sleep in their gym at night for a week(even though there was a mouse and scorpion problem there, I didn't care).

He was a cool guy, had some hilarious stories and you could hold a conversation with him for hours. He once told me he didn't learn how to read until he was 28. Said he taught himself. I asked what motivated him to do that and he said he wanted to be able to read the captions next to women in porno mags. Both my grandparents and his mother dumped a lot of cash into him but nothing helped. He would always get mad at something a leave again. One of the more memorable times, he was living with his mother for a bit (I think the cops grabbed him in Dallas and his mother was close to there) but he got mad at her for some reason and started to leave again. She gave him her car, some cash, stuffed the car with clothes, food and a TV. He drove off in it but it broke down about 10 miles down the road. He just left it there and hitchhiked to Dallas where he stayed for a month or so before getting picked up again.

He died about a year ago actually. Probably 55. He spend his last few years living in some low incoming housing (for free) near Dallas. His last year was spent with him having various hoses hanging out from his abdomen. He would have to go to the hospital for the doctors to drain fluids out of him from failing organs. He didn't seem to mind though, he thought the hoses were stupid and kept drinking until the end.

Hard to say how much he cost society (from a government perspective). He seemed to pay his way most of his life. Only the last few years did he get any kind of government assistance.

Heck of a guy, but dang.