If I've learned anything from being homeless, and my struggles against it, is that most people, nearly all people, don't understand homelessness. Moreover, they don't WANT to understand homelessness.
Even if they explore homelessness, their own ideas, own prejudices and bigotry, filter out much of the reality that is homelessness. People just don't seem to want to know. Perhaps it's all just too uncomfortable for them.
On a brighter note, I do think that compassion for homeless people is on the rise, and that is a good thing. But again, that compassion is being hampered by a certain willful ignorance. It's a bit disheartening to be in a kitchen where lunch is being prepared for the homeless, only to hear the cook and other volunteers speaking disparagingly about homeless people. (I have seen such things happen.)
When a homeless person is able to improve his life, so that he makes a concerted effort to leave homelessness, usually the first thing he does is fix his appearance - he showers and shaves and get a hair cut, he finds clean clothes to wear that are in good repair - and then people begin deny him help because he doesn't "look homeless". It is all very disconcerting.
For the vendors of the homeless newspaper in Nashville, it's a delicate balance. If they look too disheveled, people will not buy papers from them. On the other hand, if they look too well kept, so that they no longer look impoverished, people will not buy papers from them either. When a vendor makes enough money to buy himself some new clothes, it's best that he does not wear them while selling the paper, other wise it will adversely affect his business. Only when people (the general population) educate themselves to the realities of homelessness, and deal with the homeless forthrightly, will things ever really change for the homeless.