I enjoyed your story and applaud your bravery in doing something so uncomfortable. I rarely give to pan handlers —we have some many in my city — and I know that if I make eye contact I am doomed. So I stay in my air conditioned middle-class bubble.
I occasionally give to people who look like they need money or but aren’t actively asking for it. Why is it that their act of asking turns me off? (See Robertson’s note below) I guess part of it is that I see people doing the hard tedious work of begging at a hot intersection and I think that surely there is some other way they could get money since they have the ability to “work” the streets. Do they try to get jobs and fail? If the cities provided work for day laborers (like a CCC kind of thing), would that help?
The panhandlers around here are sometimes aggressive and kind of scary, and I think that it would be ideal to approach the homelessness/joblessness problem without encouraging begging. Also, what happens when everyone goes to paying for everything with apps and credit cards? That will surely have an impact on the ability of panhandlers to earn enough for survival.