Some homeless people are comfortable being homeless. They believe that they are free. No job(no boss) , no rent to pay to a landlord and have some places to go. The Reverend Al Sharpton came to a vacant lot to open a tent city for the homeless in Liberty City. There was a problem with that. The lot wasn't enough for the homeless people in Liberty City and other folks living in the area just didn't like it. These people could only live in cardboard boxes which could break down in the rain and could be set on fire by anyone who has a dislike for the homeless. And it wasn't enough for the cold temperatures. The county had a better idea. The county acquired an apartment building and offered to move the homeless in, under the condition that they find work after a few months. Some of the homeless rejected the idea because it meant surrendering their freedom.
Some people are homeless by choice. To get assistance, they pretend to be mentally ill to get a supplement check or food stamps(a reloadable card). Churches offer free clothing sometimes and even employment assistance.