There is a perception that to be without a static home is a terrible, terrible thing, but really, I can imagine for someone who appears to have his life together in many other ways (and free from other issues that plight the homeless community such as addictions) - then it could possibly be quite a liberating lifestyle.
I can of course see the other side of the equation where it would also be a prison - having to lie about his home for embarrassment etc. But in this very specific example, he seems to have got on with it and made the most of the situation