I just think there is something personal about giving someone something a "brighten their day" with an extended hand. But never to those who are obvious scammers, or even asking...
I actually think the gesture and their sincere gratitude for it might help them a bit... not the amount. I don't do this often.... it's usually spur of the moment....
And if they want to buy a $5 beer with it .... then pick a good Bastard
.