Think you've hit on something, here ...
You mentioned jails, with some disgust. I agree that just building more jails isn't going to solve any problems, but it did make me think of something.
Have you had time to see the "Cell Dogs" program on Animal Planet"? This is a reality TV show about the recent movement to bring shelter dogs with behavioral problems (slated for death)into the prisons to be trained by inmates. I've seen several episodes of this, and it's just amazing what this program has done for the spiritual growth of the inmates.
Understandably, they identify closely with the dogs. In fact, I think a LARGE part of the program's success lies in the fact that the dogs and the people have the same mindsets, and at some visceral level, they are able to relate and communicate effectively with each other. The prisoners live with the dogs 24 hours a day, and take the dogs through rigorous training programs. They know that if the dog is not trainable, it may go back to the shelter to be euthanized, so they are highly motivated to coach the dog through the problems. There is an incredibly high success rate with the dogs, and there's usually a long list of available adoptive homes for each animal, at the end.
And there's another enlightening lesson for the prisoners -- a BIGGIE that we all need to get at one point or another, in order to become stronger -- You can love something -- give it your whole heart and soul -- and then LET IT GO. And you won't fall apart. You won't crumble up and die. I don't know how, exactly, feelings of dependency like this are related to socially marginal behavior, but somehow they are. Learning this lesson with animals has been instrumental for me in my processes, and I can see through watching the program how it's helped the prisoners work beyond their criminal mindsets, too.
Allowing the downtrodden to PARTICIPATE in the helping process is probably the best thing you can do to facilitate their growth. You casually mentioned one individual in your care who took time out to make sure a friend of his got medication and food. I wonder how many of the homeless you've served have looked up to you and your colleagues, and wished that they were on the other end, helping, instead of being helped. You might begin asking for one or two of the homeless to help you distribute food or blankets, or to get the word out about certain new services, and then go from there. At the very least, your trusting them with these jobs will boost their self-esteem.
Trust is the most amazing thing, isn't it? "Jean Valjean, my brother" You bestow it upon people and they often become worthy of it.
Anyways, the thing with the dogs is working in the prisons, and I hope that it spreads. Prisons OUGHT to be not only a place of confinement but a place to grow spiritually and mentally stronger. The Cell Dogs program is one of many examples of how animals are excellent therapy for people. One of the reasons I am excited about my decision to work with animals is that I believe they are able to reach places inside people that all the HUMAN compassion in the world cannot touch.
How about trying something like this in your homeless shelter? Start a partnership with a local animal shelter and bring some of the dogs in to be trained by the homeless men. I don't know how feasible this would be, but it's an idea. Check out the Cell Dogs thing. It WORKS!