Actually, in New York you pretty much have to
try to be homeless. I'm not going to say that being hard-on-your-luck is a breeze in New York, but with things like City Harvest (a truly brilliant concept --
http://www.cityharvest.org/), the anual coat drive, and the city's homeless outreach programs, it's certainly a lot better than many places. There was a good story a while back on "This American Life" that talked about this subject (
http://www.thisamericanlife.org/radio-archives/episode/358/s...). Additionally, you have Geoffrey Canada doing his thing up in Harlem...one of the true innovators in social reform. If you haven't heard of him, go read everything about him that you can
now!
Honestly, the biggest gap in the city is caring for the mentally disabled. A large portion of the city's homeless population are schizophrenics, and they will effectively never be able to be productive members of society. For them, the only solution is long term care, but the city's mental facilities are really horrible. Unfortunately, the public's views on mental illness are still stuck in the 1890s...