It’s a tough call. I used to give a dollar to every guy on the street corners figuring it wouldn’t add up to much. Then one time we were at some food stands and someone claiming to be homeless and hungry approached us. We bought him some food at one of the stands. He sat down and promptly dumped it in the trash a little later. He maybe took one or two bites at most.
I sat in on a couple of presentations about the homeless and found out that most of the truly homeless are a bit schizophrenic and are afraid to come out in the open. Many of the folks who claim to be homeless aren’t.
Now I give to the soup kitchens and help agencies, and rarely give to the corner panhandlers. I still feel sorry for folks who have to beg to make ends meet or feel that they have to rip people off to get ahead in life. One of the local news agencies followed a panhandler, who got into a decent car and drove off when he was done. He probably had a nice home too.
Some years ago, a local disabled person who used to sit on a DC street corner, was found dead in his Florida home with several hundred thousand in cash. He owned a bar in DC and just sat at the street corner because folks would toss him money even though he never asked for it. I remember tossing him a few coins when I was a kid too,
But even if the guy doesn’t really need it. You should never feel bad about giving. It’s not your fault if the guy was just greedy instead of needy. And in the case where the guy was really a poor person, you did a good thing. It a shame some folks give poor people a bad reputation. They have their own sins to answer for.