I get it, but $5 to change someone's life?
It's funny there was a moment I was at a bus station, somebody asked me for money and I dumped all the coins I had in my wallet in their hand for future bus rides. And some lady comes up to me jokingly like "you handing money out? what about me".
But yeah I think I should just give the money out, I think aside from the guy at the red light that's there almost everyday when it's warm, it's rare I encounter somebody personally. Until I go into the city.
Buy someone new clothes. A sleeping bag. Utensils. A library card or bus pass. If it has to be cash, you don't have to stop at $5. I sometimes give out tens and twenties. Obviously at a place like California your altruism can be spread pretty thin; just ignore the people who are more difficult / less appreciative. Find someone who is appreciative. Get to know them and find out what is holding them back. Maybe you can't help, maybe you can. I've had people tell me I've made their day, their week, their year.