My interactions with our city's homeless population has been mixed. I once had a man in a coonskin cap spit on me in Union Square. He claimed I stared at him for too long, but wouldn't you stare at a man in a coonskin cap in the middle of Union Square? He was a bit hostile to say the least. Then there are the nice hobos like the one that hangs out near my apartment, who typically offers to help me carry my groceries. I never take him up on it, but it seems like a sincere offer and not him trying to get something out of me. Then there are the unhomeless homeless. The people that have better shoes on than you asking you for change because they lost their job, their life savings, their home, their AIDS...whatever it is. I don't have a lot of sympathy for these folks because they are ripping off tourists and taking away from the people in actual need.
Well even though I joke with you I am mildly sympathetic to the plight of the hobos. I often leave food out or give them whatever food I have on me. I once got some pizza thrown right back at me for offering it to the wrong hobo. Apparently not all homeless people want to be spoken to or offered things. I also got followed down Broadway and yelled at for like 6 blocks for smiling at the wrong hobo. Perhaps hobo isn't the nicest word and maybe making light of what mental illness many of them have also isn't nice, but I am just joking for laughs. I do feel sorry for many of them, but there is also some humor that needs to be found in it or you will depress yourself with the amount of homeless people you come across any given day in this busy city.
So if you have any trips planned to NYC in the summer keep an eye out for your neighborhood hobos, bring some extra snacks, but you can't give money to all of them (Shannon) or you will be broke in about an hour.