In the area where I work, there are quite a few homeless people. I've seen one guy out here for 9 years now. He isn't homeless because of some financial disaster. He is homeless because he clearly has a disease of the brain. He spends quite a lot of his time locked in combat with somebody in the sky. I don't think giving him $1,000 or $1,000,000 would keep him off the streets for long, if at all. What he really needs to get him indoors is treatment for his disease, but as is the case with many people with his type of affliction, he'll probably be back out here sooner or later.
"Homelessness" isn't always somebody without a home who wants one. It's a problem you can't just throw money at to make it go away. You can't just give all of these people jobs and consider the problem solved. It needs to be treated as a symptom of a disease, and one that usually cannot be permanently cured. Even if you could cure it, they are still human beings who deserve to have their wishes respected, and if they refuse treatment you cannot just force it upon them. Some people make the choice to live out there, because it's easier to cope with their disease this way. The next time you see a homeless person, please don't look down on them like some dirty bum pushing a stolen cart full of blankets and trash; they're probably suffering far more than you'll ever know, and it's most likely not at all their fault that they're in that state.