Im of the mindset that you can never go wrong with kindness. I've dolled out a few of those $20 gifts to homeless myself. It's a cool experience for both involved for sure. I've NEVER only given a verbal tip.
I hate giving my money to the homeless, nothing cool about it. I want to spend that money on myself and my family. I have a tiny sliver of understanding about how shitty their lives are and it compels me to give up a small portion of my hard earned bread to them, out of...compassion I guess, maybe sorrow. I should give every cent away if I were a decent human being but you know what, Fuck em, they probably made their bed and they will get what I give them, my shitty crumbs I guess. I've seen people who's hearts I admire more than any others give their last 5 bucks to shitty gutter punks who were traveling. I wish I were that kind if person but I'm just not. I hate that homeless people get my money but I hate the idea of anyone needing it that bad. Whole thing, my loss their desperation, makes me sick.