Without addressing structural poverty and systemic familial dysfunction why would anyone expect the problem of homelessness to end?
I don't know if I need to provide much more in terms of "analysis" beyond the headline of this entry, in response to the report earlier this week ("DC, advocates at odds over homeless families; 900 people still in shelter" from the Post) and the Post editorial ("Why does DC still have so many homeless?") and op-ed by Colbert King ("D.C. children in shelter must get real homes").
Getting "real homes" sounds simple but capabilities and behaviors required for being able to function individually and as a family makes "keeping real homes" a much more complicated proposition.
The long term solution is to deal more deeply with breaking the poverty cycle and the cycle of family dysfunction (part of this, at least in DC has to do with young parents, not organized in families, with multiple children with different partners).
Of course, escalation of the number of people currently homeless has been exacerbated by the recession that the US has been in since 2008.
During recessions more people become impoverished and it becomes even worse for those already extremely impoverished because problems escalate more rapidly when you have fewer resources at your disposal.
It's only possible with the equivalent of an internal kind of "Marshall Plan" focused on this (something I intend to write about sometime within the next few months).
Although given that jobs are settling out to be either high income high skilled or low income low skilled without much in the middle (although a big reason that there are job shortages in some sectors appear to be because the wages provided are subpar compared to the amount of skills required for the job), "fixing" this problem will take a long time because there are no simple solutions.