I travel to San Francisco for business every so often and it is a really depressing place. Everywhere you walk there are homeless people and bums all over the place. It is just amazing how many there are. It is a little scary to walk around when it seems like half the people are mentally ill and talking to themselves or yelling at you.
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Up in NY I went with some chabadniks on a miftzoyim trip. I mainly was looking for a ride to town. Unfortunately for me, the town was some backwater hippy colony. They had a reform church (shul that looked exactly like a church) and actually had things like "fortune tellers" and hippes everywhere. I wanted nothing to do with that place and hope I never see it again.
The funniest thing was when one of these Chabadniks was trying to ask a guy if he was Jewish or knew where to find any Jews, despite that the guy was clearly there to sell pot to these hippies and wanted anything other than attention.
I've lived here for many years, so I definitely disagree your characterization of the whole city as depressing! As far as the homeless situation goes, it really depends where you are. There are certainly a lot of homeless folks in the downtown/midtown areas, which is where I assume you're spending most of your time if you're on business. Further out towards the more residential areas there tend to be far less.
I don't know if you were ever in SF during the Brown years, but the homeless population has actually dropped quite a bit under Newsom, by pushing social programs (and bus tickets) over handing out blank checks. It's still not great, but the police do their best to crack down on the more violent or aggressive panhandlers and the others seem to leave people alone-- at least, that's been my experience.
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