Jordan is probably right that you are enabling,but sometimes the spirit moves you to give.
I will say there is something completely wrong eternally with somebody who is cool boldly asking people for money for nothing.
You have some people who catch you in the parking lot and quietly ask you if you have anything you can spare.
But these people with signs,standing at a intersection asking for money

?
Nah too much pride and too much boldness to be homeless,you've been doing this for too long and don't give a damn anymore.