We are a small community near the coast of North Carolina. This was our first homeless person that was sitting somewhere with a sign about working for food. People weren't keen on just handing a guy money to sit in the road fearing that it would encourage others to do the same so we found out if he was legit homeless and then when we found out that he was we came together to help him out. This is one of the reasons why I really like my small community!
The problem with the big cities is likely that the problem got out of control a long time ago and now it simply isn't possible to fix it. We would prefer to avoid ever getting to that point.