[danielsoneg]

Great response. I think you're touching on a lot of the more fundamental problems in any approach to helping the homeless.

You mentioned contact and community a few times there - do you think that dealing with full homeless communities, or at least a subset of 5 to 10 people, would be more successful than trying to deal with individuals? Do you think that choosing a group of four homeless folks and moving them into either a single apartment or neighboring apartments would wind up having a greater chance of success? Or do you think that would perpetuate social norms that are nonconducive to more survivable lifestyles?

Take this as a component of any particular aid approach, by the way - there are no silver bullets and a lack of a roof is often a symptom of many other problems that can't be solved by craigslist's housing section.