[bnk]

I don't give out money. Will give out food though. Even in the Suburbs there are a few holding signs standing at an intersection.

Ill give them one of my extra Chicago Style TM hotdogs [ I wouldn't be cruel enough to give him a plain one ] and my fries if they look really needy.

I haven't done that in the city though. But if I felt that someone needed to eat, I would pop in a fast food place and backtrack to give it out if I really thought it was needed and I wasn't in a hurry for anything.

Back in College we had a homeless man live somewhere by the greek housing street area. We would always give him our extra aluminum beer cans often several hundreds at a time after a long night.
He did a pretty good job cleaning up the houses for cans. Instead of the garbage we just bagged up the cans and left them out back. He would take those and all of the others scattered around the outside. On a weekend from several houses he could take in several thousands of cans, not bad really. He worked hard to smash them with his feet away, from the homes, to make them easier to move large quantities at a time. He never asked for money, just aluminum cans.