My husband and I used to ride the train to work into the Loop. We had the normal morning/evening Chicago commute, and we would see this Vietnam Vet in a wheelchair everyday, he did not have legs. He did not specifically say he was homeless, jut looked down on his luck. He would sit there with a coffee cup for money. He was pretty familiar to everyone. I am sure over the years, we had put a couple bucks in his cup.
One day we both commuted in at an off time, I think like 10:30 am. We are walking toward our respective offices, and we see the guy. The guy pulls out car keys for a nearly brand new Cadillac. So since we have seen this guy for years, and weren't afraid of him, we decided to ask him what gives. He claimed he is in fact a Vietnam Vet (which we never doubted) and considers the pan-handling his job. In cash, he averaged $60,000-$70,000 a year; which was needed in his opinion--since he had two kids attending the University of Chicago. He said he only sits out at the train station during his "peak earning hours" morning and evening rush; and mid-day he takes a break.
Needless to say, we were floored. It had never occurred to us to consider this to be a career.
Now I am not saying everyone is a scammer. A couple of years ago, I managed to get downtown on the train without my wallet. (I did not notice going into the city, because it was so busy they didn't take fares--happens once in a blue moon). So here I am in the Loop, no longer working in the Loop (so no co-workers to hit up) with $0. Out of desperation, I asked a cop for $5 to get home. I was pretty well dressed, and had my purse--just not my wallet. He had a look on his face, like I was scamming him; but since I asked him for $4.80 (my train fare) he couldn't decide if I was legit. He did give me the money, and I took his card too. That night when I got home, I sent him a refund, along with a healthy fee for the use of his money. I was embarrassed, but would not have started asking random people--I just asked the cop that worked at the train station.
Normally, I am a pretty soft touch. One day a man asked me for money for food. I offered him an apple and a granola bar instead. He told me he "wouldn't eat that s**t", after that I decided to leave most helping to professionals, whom I could help with donations to legitimate organizations. I really don't mind helping someone, but it would upset me to know the money was being used for drugs or alcohol.