Decades ago I worked downtown Chicago, the Loop. Used to be panhandlers at both ends and on both sides of every bridge crossing the Chicago River, as well as all over the Loop. One time going to the commuter station to head home, happened to be a panhandler by the train station, said he was hungry. I went into a restaurant right there, bought him a sandwich, came out and handed it to him, he went off on me that he wanted money, not a sandwich. Another time, used to see the same guy every morning, every evening on his corner of the bridge, and if you're a panhandler, you don't setup on another panhandlers space, or you're done. So I see this guy every day, he seems friendly. Christmas bonus time one year, I get a bonus check for over $2,000. Its free money to me, so on my way home, crossing the bridge, I give the guy a $100 bill. Free money to me, so what the heck. I tell the guy get a hotel room and a good dinner on me, and he thanked the heck out of me. Couple of weeks later, he's a security guard in the building I work in. I see him, he sees me, "Hey, how you doing...". That goes on a couple of weeks, and then I see him panhandling on the bridge again and asked what happened. He tells me that he makes more money panhandling. Across the street at the Opera House, there was a guy wearing Marine camos panhandling every day, "Can you help a disabled marine?". They'd bring school bus loads of kids to the Opera House during the weekday for weekday matinee's, and the guy would stand in front bus doors begging kids for their milk money, getting their milk money, and at the end of the day get into a Mercedes parked in a lot over on Halstead St and hit the expressway headed north to the suburbs. One day, he got stomped badly, and when the cops showed up to help him and found out why he got stomped so bad, they left and he got stomped some more. I could go on and on and on.
These days though with the economy being what it is? Hard to say. A judgement call one has to make on their own. Chicago jaded me since I used to see the same guys on the same corners day after day, year after year, when the economy was smoking good for anyone that wanted work and as much work as they wanted. These days as the economy is taking off like gangbusters, so we are now being told? Judgement call. Good luck.
Mark