Brian, Good of you to notice this guy's situation, be a good listener, and have enough compassion to post this to the board. A housing alternative might be an older used motor home or travel trailer; only catch is he would need to park it at someones house. RV park rent is quite high. If you can find someone willing to let him park a rig, hook up to water, power, etc. then I could contribute to the cost of an RV. Once he is on his feet, the unit could be sold, and the $ either gifted to him, or distributed to the original investors...Here's a real cheapie: http://flagstaff.craigslist.org/rvs/4710631373.html
There's many others in the 2K dollar range that would keep someone safe and comfortable for some time.
Let us know if this might be an alternative.