Having been around so much poverty, both in the USA and abroad, I just go ahead and help people. So what if the bum in the street is going to take what little change you give him to buy a bottle of Ripple? Sure it's not good for him. But at least for a short while later in the day he or she will have a bit of respite (albeit in a drunken haze) from the daily Hell he or she endures.
I grew up in a religious community and State that had big things to say about charity and caring for "our brothers and sisters", but the barrier was quite clear that only those officially recognized as "brothers and sisters" were to be offered any kind of help or be trusted. I also remember how much better things were for the mentally ill and impoverished BEFORE Herr Reagan began his dismantling of the public safety net systems for the indigent and dispossessed. Anyone else remember the month shortly after he was elected when funding for public health services were slashed and suddenly the streets were full of newly homeless? If not, you're blind as well as stupid.
Even more shocking to me has been the few times I've been with friends I assumed were somewhat enlightened only to watch them yell and scream at a homeless person who asked them for 25 cents or a Dollar. Sure, you're going to get ripped off now and then, but more often than not you most likely will be spreading a small bit of positive karma.
A woman rushed up to me in a supermarket parking lot one afternoon begging for money to buy Kotex. I gave her a couple of dollars and she ran into the the store. While I was shopping I bought a couple of boxes of Kotex just in case I saw her again. I never did. She was probably scamming me. But a couple of weeks later those boxes of Kotex came in handy when I picked up a complete human wreck of a woman walking along on I-80 in the middle of the desert who didn't know who or where she was. She was filthy. But I endured the smell in my truck and drove her to the local women's health clinic in my little town in Nevada. The County Nurse was very happy when I presented her with those boxes of Kotex after handing over the lost woman.
Whenever I'm back in the USA I drop off regular offerings of soap, toiletries, hand cream, and a few "clearance" item blouses, women's pants and T-shirts to the local shelter. The Hell with giving to some professional charity group that is going to take a 25% cut (for administrative purposes) before they hand out the rest of the dough to non-profit charities who need the money.
About the only group I do not help directly are the professional gypsies who work the Metro cars in Barçelona and other large cities in Europe. Roms have their own culture and as fascinated by it as I am, I cannot bring myself to directly support it. When pressed, I hand them any loose USA change I may have on me. They look at it, know that it's money, but don't quite know what to do with it. At least I give them something.