I posed the same question to family members and here is what my brother said. He's the one in Chicago.
"Having worked in downtown Chicago for several years, I've had my share of encounters with panhandlers - some quite funny, actually. I made an effort to get to know some and would occasionally treat one to a Burger King or something to sit and visit with them. There was also a group of homeless people that built their own little camp on an abandoned loading dock near the hospital where I worked. I would often spend lunch with them, taking them leftovers from a lunch meeting. What I learned was really most interesting.
There were some that just hit hard times and did want to get a job, and were actively looking. They would panhandle between odd jobs and job interviews. These were usually pretty easy to spot, as they were usually well kempt, clean, showered, clean clothes - it was apparent that they were sincerely trying.
There were your stereotypical drug addicts and alcoholics - dirty, stinking of stale booze, festering body odor, and dried urine. These guys would sleep wherever they happened to pass out - maybe on the sidewalk during rush hour with business executives, salesmen, and secretaries having to walk around - or over - them. Some would at least have the courtesy of making their way to their cardboard home on lower Wacker or lower Michigan Ave to pass out. But it didn't smell very good down there.
A significant percentage of them turned out to be what I called "professionally homeless." Homelessness was their chosen lifestyle, and they actually considered panhandling their "job." Their freedom from any obligations to others was more important to them than food and shelter. They learned how to survive on the streets, where and how to keep warm in the winter, and where and how to keep cool in the summer.
In talking with homeless people, I would ask them what percentage they would guess were professionally homeless. They would consistently give me a percentage in the 90s - over 90% were homeless by choice. Of course some of this percentage also included some of the druggies and alcoholics. Some of the druggies and alcoholics were not homeless by choice, homelessness being a consequence of their substance abuse. But some were both - substance abusers and homeless by choice. Others were homeless by choice, but not substance abusers.
Through getting to know them and learning who they are and why they live the way they do, I came to this conclusion that might help you, Tony. I learned that if they are choosing to live that kind of life, it isn't my place to pass judgment on them. But nor am I obligated to subsidize their chosen profession. I am not their employer - I did not hire them to do what they are doing. Therefore, I don't owe them a wage or salary for their panhandling efforts.
So it's a trade-off. I don't judge them, but nor am I obligated to help them.
But there's another side to this. I have encountered the occasional bum who tried to impose upon me an obligation to help them. They would pester, threaten, and pass judgment on me if I didn't give them what they wanted. I was going to give one guy 5 bucks for a bowl of soup. He looked at it and said he wanted a steak dinner in the restaurant we were standing in front of, so that wasn't near enough money. I put my $5 back in my wallet and walked away, his curses echoing through the streets behind my back.
Then there were a few occasions where they would ask me for money for a sandwich. I told them that I didn't have the money, but I did have a sandwich and would hand them the sandwich Sally made for me for lunch. They'd look at it like it was a moon rock or something and walk away. I guess it wasn't the kind of sandwich they had in mind.
There was also the guy that would sit all curled up in a hoody with the homeless sign in front of him asking for help. He had the pathetic look down like a real pro. He would look up on occasion with big, sad eyes like a beat up puppy. I happened to run into a homeless lady from the loading dock group. She wanted to introduce me to a new friend of hers - the pathetic guy. When she introduced us, he jumped up, shook my hand with a big, friendly smile on his face. As I was turning to leave, he resumed his pathetic position and went back to work.
If someone chooses to be homeless, and if I choose to treat them to a burger or something, it will be on my own terms, not theirs. I owe them nothing, and they are in no position to obigate me to give them anything at all. I won't pass judgment on them - and I expect the same respect from them.
Hope that helps put things in perspective for you."