Yes I am. There is one gentleman who is around fairly regularly, he doesn't have a permanent home and he is fiercely proud of that. He has money to buy stuff if he wants. He likes to read and will often trade books with the used book store or ask for books from garage sales as he sees them. He was reading one Asimov's Foundation books when I met him sitting next to his stuff.
We don't get as many outright beggars but occasionally we do. One person I talked with who was simply demanding cash I suggested we trade stories. I'd tell him a story and he could tell me a story. If we agreed he had the better story I would give him $6 (which is the price of a typical paperback book). I told him about the birth of my daughter and how it changed me in ways I didn't expect. He told me about of joining the Navy rather than being sent to jail for shoplifting, and learning the fastest way to clean a mess hall that had just fed 80 sailors who had been sea sick. I gave him the $6. But strangely he didn't really want it, he wanted to tell me more of his stories. But I was out of time so I said if I saw him around again I would ask for another story. Sadly I didn't see him later. He really was a pretty good story teller.
The people who have been problems have either been high (drunk or drugs) or mentally damaged. No fault of their own but they simply weren't in a place to be human. My wife and I called 911 and helped one guy get to the hospital, he was passed out in the parking lot of Safeway. He didn't appreciate the help but I continue to feel it was the right call.
I am. I look them in the eyes and treat them like people. I know from the people I talk to that the worst part is having everyone ignore you and not treat you like a fellow human. It breaks my heart. It sucks out there. We might be off topic but I get you.
One of the problems in activating the homeless population is that they're not a community - most people have a life situation, lose their shelter, have a rough time, get back on their feet, and then can afford to rent again. There are some who live without permanent shelter perpetually, but this community is a small fraction of the overall population, and they have different goals.
This is a genuine question. How do you interact with people who live on your street but do not have shelter?