Dear @rok-sivante, many of the struggles you had put amazingly into words

"It's always been a very uncomfortable emotional response when seeing these people. Part of me feels sorry for them at times. Part feels guilty for not giving them anything. And there's been this pending sense of guilt even if I were to give them something, as though I'd be enabling them, supporting undeserved handouts, and contributing to the "problem.""

Are very familiar to me. I don't even think I can put it in a better way than you did.
Lately I was also braking this habit and sometimes giving whatever change I have. Still, again I'll borrow your words:

" And when I walked away, I didn't feel any sense of smug satisfaction at having done a "good deed." Hardly. On the contrary, I felt a pang in my soul, disturbed not only by how painful of a position this person has landed in, but also that there was really so little else I could do - seeing the man's suffering, but unable to change it."

I remember few years back (around 2013), I volunteered with a group of people that were making efforts to help homeless people by providing some healthy and freshly cooked food (They used to cook burritos) as well as some essentials, like socks or sanitary pads etc.
After we are done cooking, assembling and wrapping the burritos we will split into groups going to different areas in Montreal, Canada to distribute them. There were many types of homeless and beggars. Some where just ungrateful and bitter to the point they will refuse the food and demand money instead, while others were touched by the small gesture and were very happy to have a meal during that day of their life.

What was very sad, however, was the fact that some of these homeless beggars were young people who had extremely abusive families (Sexual, physical and psychological), that they chose to live on the street and humble themselves to the outsiders rather than to stay home and accept the abuse from their relatives. That is, despite the possibility that they will be abused by outsiders as well.

Such heart wrenching reality was mind changing for me and a reason why I chose to break my habit. As I came to understand that I don't know, and probably I will never know, what these people went through, how much they suffered and what made them break down to that point. So it is really not up to me to arrogantly decide whether they deserve my help or not.

Since then I decided that if I crossed paths with someone in need and got the feeling to help them with the little I can (at least by acknowledging them with a smile) then I will do it.
More importantly, I decided that I will not question anymore whether I am doing the right thing or not, but I will pray that they will get the best out of my help

Many thanks for sharing your experience which allowed me to share mine. I still think you are a good person at heart (even though you don't want to be praised) because at least feel bad if you don't help enough or at all :)

Love and peace :)