I read somewhere that Denver has the highest homeless rate of any US city. Not sure if that's still the case.
There are few panhandlers near my place that do quite well for themselves. One is a guy in a motorized wheelchair that we call "Buck". He parks outside one of three or four businesses and always says "How about a dollar?" (Thus the name.) He lives three blocks from me, in a building nicer than mine.
There's a guy in his 50s, surprisingly clean-cut, who has a story about "falling on hard times". Once, I gave him $20 and told him "Look - I'm free to the line now. You don't ask me for anything anymore." He said "I'm going to pay this forward - thank you so much!" Three days later, he hit me up again. I told him "Dude, I gave you twenty bucks three days ago." He smirked and said "Nobody ever gave me twenty dollars - you're a fucking liar." He still hits me up to this day.
Sometimes, I'll try the tactic of buying them something. I don't mind adding a burger or something to my meal, and handing it to them on the way out. But I've had guys go into the restaurant with me, and just start ordering. One guy literally ordered over thirty dollars worth of fast food. After he finished ordering, I just said "OK, you got this one" and walked out, leaving him to pay for it. Not sure what happened after that.
I mainly donate to the shelters in town. They tend to do a good job. There's also a place nearby where you can volunteer to work - cooking or cleaning - in exchange for a meal. I tend to send people there. If they say "no, just give me money" then I tend to cross them off the list.
Lex