I was getting my car worked on and there is this place across the street which makes great NY style stuff (Portland, OR) and I went over for a couple beers and some garlic bread. Overheard the waitress stressing about stuff talking to another person she seemed to know (real family joint). My bill was $11 and I tipped $20 with a note that said "happy bday!" because I overheard she was sleeping in for her bday but then had to come to work.
Also, had a full suspension mountain bike I could have probably gotten $450 for on CL, but it was a gift to me so I drove downtown with it on my bike rack, found a homeless dude with the worst bike and gave it to him. He cried, I cried, we all cried. The rest of my day was great.
I'm actually thinking of ordering some sub-zero sleeping bags and handing them out downtown but have to see where my finances fall.
I've tried giving packaged food to homeless people before -- whatever I had on me, like a granola bar or something. They've always rejected it, saying they wanted something else. I'm not sure how someone in their position can reject something like free food. Really put me off.
There was a thread on reddit asking "past homeless people, what can I give homeless people" and it was strange but food wasn't necessarily always at the top of the list. They say that most can get meals or are in places where they can be fed, and that you don't just 'eat' a lot, you eat very little and adjust to that. With packaged food they'd have to carry it around so while 10 cans of Spaghettio's seems like a great idea, they risk being robbed by people who don't try and get fed in other ways or having to carry it around/hide it for a day where they can't get fed and will need it. Blankets, sleeping bags, socks (OMG socks!) were some of the top things, for those that aren't "permanent homeless" and trying to get out of a rut or w/e, showers, a stay at a hotel for the night, deoderant, toothpaste/brush, etc ...
It was a really weird thread to read. When it comes down to it money is probably the best thing, while you run the risk of giving to the wrong person, it's the one thing that they can hide/stash rather easily and be able to turn it into something they need later.