Let me be gentle about this. I think Craig is primarily looking for someone with the skills to practice dedicated work. Homelessness develops one's skills in different areas. I don't think working long hours in ag country would be a good match for big-city homeless folks.
You mean to say that homeless are lazy and have no work ethic?
That's true of most homeless, I think. But a small minority of them probably are good physical laborers who just lack the ability to find good jobs. I wonder how one could weed these out of the general homeless population.
Unfortunately, a sizeable percentage of homeless also suffer from mental illnesses that directly impact their ability to hold down a job. A friend of mine who works at a metropolitan hospital constantly sees homeless people there, by their entrance not to beg but because they want to be admitted, to get treated, to get off the streets.
I'm only speaking about the experience, not the people themselves. If you want to learn how to live workfree (I think that may actually be a thing) in the US, being homeless on the streets of Santa Monica would teach you a lot. But if I was Craig, I'd be looking for the guys who work at a Hormel plant in Kentucky instead.