I like to help, but I am VERY cautious. I’ll help at soup kitchens, where they eat the food right there and you know it is helping. I helped one guy regularly for several months, where I would get buy-one-get-one-free sandwiches from a major chain (I had a hundred coupons) and give the guy one of the two sandwiches - and he would start eating it as soon as I handed it to him. Give a homeless person anything that can be re-sold? Not in my opinion a good idea.
Rather than give money, I used to always buy someone panhandling a meal and bring it out to them. More than once I was cussed out and had the food thrown back in my face. Food wasn’t want they wanted. I don’t do it as often anymore.
even your system doesn’t work if you think it through.
take random homeless drug or alchohol abuser, he spends a few hours panhandling ... and now has enough money for some food....
he is getting hungry ... but he is also starting to need his next fix...
along you come and give him a free meal!
now he is free to spend his money on that crack he has been jonesing for!
There is almost no way to help anyone without simultaniously inabling the bad behavior that probably got them to that position in the first place.