I've always been torn concerning giving money to beggars. Sometimes I do and sometimes I don't. I don't see them often in the Go as I did in DC a 15 yrs ago. This article from Relevant speaks concerning that topic although it comes to the same conclusion I usually have: it depends.
I'm of the opinion that money is not my own. I'm only taking care of it and eventually through the economic forces it will either tranfer to somebody else or turn into something. A weird definition but true I suspect as we don't use dollars or cents in that great beyond.
One book that opened my eyes up more to homelessness was Under the Overpass. I actually saw the author in the Go a few years ago. But the discoveries of 2 young men who decided to become homeless were insightful and compelling. I don't remember what the authors said about hand outs but they seemed cautious as they encountered many on streets who were there because of poor choices (drugs and alcohol abuse). A third category they encountered was the mentally ill and that's probably the hardest to deal.
So the tug of conscious is am I using this money, that is not my own, by giving to some who may or may not use it well and thus heap condemnation on them and myself. Whether that is completely true I am unsure. It has been written that the love money is the root of all evil. So in a manner money has power- to do good or do evil. (Or will my change, love has power.) For money some people will do anything. I digress before I get in a complex Kantian debate here.
I am convinced there is evidence for both sides and so the concluding remark remains - it depends.
But maybe on a wiser note- perhaps gift cards or certifcate could work better. Sure it could be sold for cash, but at the same time there is that possibility it will be used. Who throws money away even if its not cash?
(Note: I forgot about the love of money thing so that changes things a smidge. Small question- how can you tell if you love money- if you are always busy or saving too much?)