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OK, what do you think they can do with the $50 that they manage to accumulate that will seriously benefit them?
That's kind of an impossible question to answer because the "they" is unknowable in your question.
But maybe they buy alcohol and drugs with it
Maybe they buy some medication they need to survive
Maybe they have a dog they want to buy food for
Maybe they have a family that could use the $50
Maybe they go to a thrift store and get newer shoes and socks for the winter
Who knows what they do with it but really $50 can help a great deal and unless you know the person well it's difficult to know what they need it for. This isn't to take away from what you and your wife have done, that is admirable and needed help too
Exactly. The easiest thing to do is ask them what they want. Personally when they ask for money, I tell them I don't hand out money and ask them if there's something else they need. It is a good way to actually have a conversation with them and get them something they need.
I also want to be clear, I'm not going to judge anyone for giving money to someone in need. It is better than not trying to help at all. I just personally believe it is better not to give homeless persons money.