I’m on the fence about giving money to homeless people on the streets, but am all for donating to / volunteering for organizations that help them.
My reason starts with how organized and strategic they can be. For example, I was waiting at a bus stop downtown and there were three homeless people planning out which intersections they were splitting to next and how they were going to divide the total afterwards.
Second example in downtown. There’s a guy begging for food in the mall, so I take him to the nearest food stand, we both order a meal, and eat at a table. He was talking about his plan to get off the streets and all and went back to refill his drink after eating. During that time, I went to the cashier for something and she told me he’s with a few others that come back pretty regularly. When we get back to the table, he then tells me that he needs $10 for a place to stay for the night and then leads me to the nearest atm. Once we’re there, I tell him everything the cashier told me and he doesn’t say anything with an “ok you caught me look”. I still give him the money even though he knows that I know he’ll be back doing the same thing.
I know this is is not the case for all homeless people, such as the meal I had with one with mental disabilities, but it’s a mixed bag. Just do what you can and don’t feel bad if you can’t.