I have in the past. Am so broke now I have nothing to give. Here in Portland, we have an awesome place called Sisters of the Road Cafe. People can buy "meal tickets" for $2 each and hand those out to street people. The street people can then go to the cafe and have a healthy, hot meal. http://www.sistersoftheroadcafe.org/
Portland has a large homeless population. Those we see are not all there is. I have been homeless as a child and as an adult. As an adult, I've been lucky to have family. It isn't fun, it isn't an adventure, it isn't something a sane person knowingly chooses. There are programs, yes. There are shelters, of course. But the need ALWAYS exceeds the resources. Shelters always have to turn people away on the coldest nights of the year plus shelters have their own dangers.
When I had a bit of money, I would buy a cup of hot chocolate or a couple of burgers if they looked hungry or cold. Or a can of dog food if the person had a dog with them. The street kids are especially a soft spot with me, the girls in particular. I cannot think of a less safe place for a young girl to be than on the streets. I know it is unsafe for the boys, too - the girls just get to me more.
When you live around it, you learn to discern the scammers and liars from the real thing.
So many of us are just one paycheck away from homelessness. There are many more poor people than rich people. If we learn more about it, we can learn of ways to minimize it.
So, my answer is sometimes, depending