The way that his entire grouping questions events is kind of dangerous. Not that questioning events in of itself is dangerous, but how simplistic their assumptions of the world are while doing it, is. None of his thoughts and questions are actually original, they're all generated by the right wing information echosystem he inhabits. In their world there's no such thing as expertise, there's no such thing as rules. Every little thread they can pull at to unravel people's faith in society and it's institutions get pulled at and it all ends with a polticial and societal nihilism that authoritarians thrive in (this is literally the Kremlin book on how to create a passive and apolitical populace fwiw and has been for decades, inB4 'lolz russia hoax').
The only way to deal with that imo is combatting it directly with accurate information. There are a lot of people susceptible to their mode of "thought" but what is bullshit has to be called out as bullshit. Do I expect to change his mind? No, not a fucking chance. But I answer shit like that so that someone else reading it here (our lurkers are a much bigger group than our posters) who see one of his questions and think it makes sense, get the issue answered with relevant and accurate information and isn't persuaded by shitty open ended questions with an inferred conspiratorial answer.