Last year on Dateline or 20/20 they watched this man do the same thing in LA (panhandle) at one of the busiest, wealthiest intersections.
They filmed cars giving him BIG money (lamborghinis etc). Then after rush hour was over, he went and got in his explorer (changed clothes ON THE STREET) and went home.
However, here in Fresno there is a homeless man who always was cleaning windshields (I use the term cleaning loosely, LOL). One day I invited him to go into the restaurant and eat with me. Man, the looks I got that day. Young, good looking prof. woman eating lunch with a bum.
He and I have become 'friends' and I do give him things I think he needs. Last summer his bike was stolen by some thugs, so Rotary gave him a new bike, and I bought him a titanium lock.
Also, down in SF last winter my daughter and I were rollerblading and we stopped for a bowl of chowder (and MAN was it cold). A young homeless man kept eyeballing us (he had on NO SHOES) anyhow when we finished just as we were getting ready to leave (he had asked all sorts of people for food) he asked if he could have our leftovers.
I told him no, he couldn't, and threw them away. Then I told him "You are not my dog, if you are hungry you don't eat my leftovers. I will buy you whatever you want to eat." Then we walked over to the vendors and he picked out about three things and paid for it, and the vendor knew this guy so he REALLY filled up his chowder bowl and told me thanks also.
So anyhow we kept him company for a few minutes, and I could tell he was mentally imbalanced. Just before we left, he had a moment of clarity and said, "You are so nice you remind me of my sister."
Well anyhow, after I got back to the hotel, I remember that I had my cell phone with me and I wished like anything I had asked him if he wanted to call home. Maybe someone was looking for him. I will always regret not asking if he wanted to call home.
As a general rule, I don't give bums money.