I come from money and when I was living in Los Angeles many of my friends were also affluent, we would go to Costco and buy enough snacks, sandwiches, and water bottles for 300 to 400 people and make bags that would feed a person for a day and keep them hydrated enough, two water bottles a person and a paper bag filled with granola bars, ham sandwiches, dummies, cookies, crackers, pieces of fruit that had thick skin, etc... Then we would go down town every Sunday evening and go to where all the homeless would sleep and hand out the bags and water. So much better than giving people cash, we went to them instead of them coming to us, we split into groups of 3 or more so it was safe, they were super grateful, it only took a few hours to make the bags up and hand them out, they could expect us every Sunday evening so many of them knew to be there to get the food and water, many of the people were mentally or physically disabled and unable to work or were illegal immigrants who came here for a better life and failed to find it and couldn't speak english, there were some families so the kids got to eat. Great thing to do.
I sometimes keep $5 McDonalds gift cards in my car for homeless people. I really enjoy talking to homeless people and will bum them cigarettes buy them food and chat. I used to smoke homeless people up back when I was a pothead, they appreciated that generally. I'm okay with buying a cheap pint for a homeless person if they're willing to admit they want alcohol. As long as they aren't aggressive or definitely trying to scam me I want to help if I can, a person is a person is a person and no doubt if a person is living on the streets or in a shelter they have needs that aren't being met and I enjoy helping when I can.