I look at it like this: How do we KNOW whether or not the person asking for help is legit? I would rather err on the side of giving a helping hand rather than turn away someone who perhaps is really in need. Of course our Me, Me, Me society would readily disagree. What goes around comes around.
I am not as charitable as I should be.
One time I saw a group of teenagers come into a Chinese restaurant with $100 bill that their mother gave them. I secretly paid for their dinner and had the waiter tell them to do a better job hiding the $100 bill in public places.