I've only skimmed over some things so I'm not exactly in any position to judge but he seems a little like an ayncap who's attracted to conspiracy theories. If he's actually as open minded as he wants people to think I can't see it being too hard to have an actual debate with him if it didn't devolve into him circle-jerking with his own theories and rejecting everything else. If I had to go with his idea of the "one true divide" I think it has less to do with the state so much as unquestionable, imposed authority.
He should look into how Capitalism functions, question the legitimacy of private property, at least look into basic marxist economics (https://www.youtube.com/user/brendanmcooney), look at the history of how capitalism was implemented (primitive accumulation, enclosure etc.) and take his ideas down to their basics so he can discern the facts from ideology. Stirner may do him some good in that regard and I think he could be interested in philosophy post Hegel with the shift of legitimacy from godhood to the "Human"/citizen etc..
>>6450 for explicitly Capitalist discussion btw.