alt Hacker News> I buy people lunch and sit on the curb eating with them and attempting to understand them.
I clearly don't have the same people on the street as you do. You should not be just sitting down and having lunch with people who are having daily psychotic breaks or are otherwise aggressive. You can't have a conversation with someone who is constantly riding the line of ODing. I have a regular I see who runs around in the road screaming at cars and people.
The very incomplete "down on their luck" view of homelessness is killing progress in my city.
I have lived in many metropolitan areas and have seen the gamut of homelessness. As I mentioned in a downline comment, the trick is to ignore the people who are not in a position to receive help, and actively seek those who are in such a position. I am not suggesting walking up to random homeless folk in San Francisco who are tweaking out and hanging out with them. I am not suggesting to risk your safety by approaching the first person you see. You live in your area; study it, pay attention, and over time you'll start seeing some familiar faces. This has worked for me in New Orleans, it worked for me in Texas and worked for me in California.
So I'm willing to bet that my understanding of homelessness is more nuanced/holistic than even yours. I have been homeless. Have you?
What progress do you feel is being hindered by a collective display of compassion?