I am homeless and have had a class on homelessness and these are two of my websites:
http://whathelpsthehomeless.blogspot.com/
http://sandiegohomelesssurvivalguide.blogspot.com/
I also started a Reddit recently called Housing Works and I have various related little blogs, like Project SRO. I am still kind of throwing things at a wall and seeing what sticks, but the San Diego Homeless Survival Guide is a thing I started for myself in order to keep track of useful info I needed while homeless in downtown San Diego and I abandoned it after I left downtown. It was not updated at all for six months and then I realized it had organic traffic. It has the most organic traffic of any site I run because there is need for the info.
A lot of people who have spent time homeless are ashamed of that fact and don't volunteer that information normally. Even those who are not ashamed and not actively hiding it, well, you don't know just from looking at someone that they used to be homeless. Lots of people do get off the street. It is not a permanent situation for everyone.
However, homelessness has been on the rise nationwide for some years now and it does concern me that there are larger forces at play here that are causing it to be more of an uphill battle than it used to be.
2/3 of the chronic homeless have mental or physical disabilities. 1/3 have drug problems. You are talking about 83,000 people in a population of 320 million, but these 83,000 people are creating huge quality of life problems in all of our major cities. In San Francisco, you have 300 million dollars spent fighting a problem created by 2,000 people. The non-profit and social services mafia employs more people to "care" for the homeless -- or more cynically exploit them -- than the actual number of chronically homeless.
First, we can go after the low hanging fruit of helping people who are more easily helped. More availability of actual affordable housing would help with this issue. Some people who are homeless do have income, just not enough to pay for a middle class American lifestyle.
Second there are things that work to help rehabilitate people with serious, entrenched personal issues. I raised and homeschooled my two gifted learning disabled sons, one of whom has the same medical condition I have.
I know quite a lot about this problem space and I see it as solvable. It will take time, but it can be done. Writing people off as hopeless does not help the problem at all. It just compounds it.
Your endeavors seem promising.
Best.
There's a Star Trek episode that explores this idea. http://memory-alpha.wikia.com/wiki/Sanctuary_District
It's difficult to think of ways of combating homelessness. To get them on their feet, you might need to redefine what a job is. A normal job requires some common elements: a shower, the ability to be there on a regular schedule, some productive task to do. But homeless people don't really have the ability to do any of those, except perhaps show up during regular hours.
It's hard to shake the feeling that the only solution is to give them money, and that most of them will just spend it on drugs or alcohol. But that's too heartless of an outlook. Some people who fall into homelessness are just like you or me. When your family connections fail and you have a debilitating illness, homelessness tends to result. And those kinds of people could be pulled out, if only we could figure out how.
There are homeless people that are essentially unsalvageable, though, and it's hard to know what to do with them. No family, no home, but most critically no willingness to help themselves even when given a small opportunity. But they still have friends, and if we focus on helping their friends out of homelessness, they might want to follow.