Aren't you hijacking the topic of homelessness here then? When people say homeless they don't mean someone who is homeless out of choice and can get out of it whenever they want to?
Probably the best thing we can do for homelessness is to not see it as a problem of "others", but as a continuum with a self-sustaining end that anyone could end up at.
Wasn't his original comment about how his (atypical) experience not living in a house gave him a bit of an insight into some of the issues that "real" homelessness creates for people? I don't see anywhere that he claimed he was just as disadvantaged as the average homeless person or anything like that.
I think your comment was informative. It kind of reminds me of "There, but for Fortune", by Phil Ochs:
Show me an alley, show me a train
Show me a hobo who sleeps out in the rain
And I'll show you a young man with many reasons why
And there but for fortune, may go you or I
Especially in countries with (dare I say) primitive social security, going intentionally homeless could quickly become a permanent thing. A broken down car and a medical emergency, a family tragedy -- and coming back might suddenly become an insurmountable obstacle. Difficult to get a job without a place to stay, difficult to get a place to stay without money, difficult to get money without a job...
Did you want to be homeless? There are SO many people that do not have the opportunity or education or resources you do. And yet you choose their poverty. Why?