Consider the methods he suggests for retaining shelter: * Squatting. * Couch-surfing. * Living in his car. * Buying some out-of-the-way land and building a house on it (which, you note, he hasn't actually done).
Two of those are blatant parasitism, the third is borderline tragedy of the commons material, and the last one appears to support the institutions he claims makes you an "idiot" for supporting. I'm sure that his friends and family that he's stayed with enjoy being called "idiots" for buying into the whole concept of property and having couches to lend.
There's nothing wrong with dumpster diving or couch surfing, but it's pretty arrogant to claim that doing so and rejecting conventional social order is the measure of an enlightened mind, when neither dumpster contents nor couch would exist without that order.
His response to criticism appears to be mainly sophistry and further reiteration of the "property is theft" meme.