I've been in danger of homelessness. At one point, the only place I had to stay was a hospital bed and would have been out on the street if it weren't for a friend who let me sleep on her couch for a summer. So I have never really felt all that different from them. They are people who have generally had rotten luck in life, or made bad choices that hurt them more than is fair, and in general there's not too much different between them and me.
To be honest, I'm not actually good at telling whether somebody is homeless. There's no guarantee somebody who is actively begging for money is homeless, and if you were and weren't begging, wouldn't you want to hide it as much as possible to avoid being targeted by criminals and run out of places like so much trash? I figure, people is people, and that's all there is to it.
I am not all that sure about what to do if asked for money. Sometimes I say yes, sometimes no. Generally the "no" is more like "crap, I'm overstimulated enough going shopping, no more conversations now please go away!" than "you'll just spend it on booze".
The moral quandary of whether or not to give money if they will just spend it on alcohol, though... that confuses me. Obviously that is their choice, but there's no way I'd ever be able to tell just looking at them which choice they would make. So I consider that point largely irrelevant. Mostly it is, "Do I have enough energy left over to deal with this unexpected event?"
The glove idea is great. You're right, not too many people would refuse those, and they wear out quickly when you wear them every day anyhow.