Sometimes I give money, sometimes I give food or something. If I can give, I try to give something whether they are pro's, or legit in need. I figure for myself it's not my place to judge who "really" needs it or who deserves it. If I give when I can, I also hope God will do the same for me even if I don't totally deserve it. I know some of the people I give to don't really need it.. but like Duck said, who knows, you might see the dude sleeping in a ditch when you thought they were scamming you.
I love Zulu's giving of fruit in S. Africa. Even here I will give food of some sort instead of cash or diamonds.
I guarantee "Black Santa" sleeps in his dirt patch in the grass that now grows moss because he chooses to. That one doesn't beg and actually loathes others giving him anything. He doesn't need to beg either because he is taken care of by society, but he chooses to live on the streets. This is the same story with 99.74xx% of humanity inside Utahs bubble.
I get the hippy mentality with karma and not judging and all, but that's not for me.