He has ten acres in Eastern Washington that he has an orchard on and is planning on building a cabin on. If/when the society collapses, there won't be any shortage of clothes, he could always just walk into a department store and take some, because no one owns them anymore.
Subsistence farming is a totally different lifestyle than dumpster diving and couch surfing, and I doubt he's much more prepared for it than your average "wage slave".
Raiding deserted department stores is fine for a few years, but that's not a long-term strategy. When the department store building collapses because nobody's maintaining it, and when the clothes run out and the factories aren't making any more, what then? Same with bicycles and any other technology he likes to use.
