One classic Gmax thing is to make every statement interpretable in a safe way. For example, today's reddit post where someone was accusing Peter Todd of being biased against an increase because of his affiliation with Viacoin. I don't think there is much merit to the accusation (though that doesn't excuse Todd's sensationalism), but in Greg's reply he said, "
Welcome to Reddit, 'Viacoin66'!"
He will say something that looks safe and unantagonizing (just the standard Reddit welcome), but his real purpose is to point out that the account was bran new and imply that it was obviously created to troll Viacoin/Todd. He's probably right about that, but nevertheless it's an example of what I mean where he'll say whatever serves any sort of low-blow purpose in a debate as long as it can be interpreted as not being that. I guess with his security testing mindset he has become Mr. Plausible Deniability.
You almost got it.
He is winning the "I am the smartest dude here" argument to himself. By obscuring his point, he further proves to himself that he is smarter than everyone else that misses the point. And those who are smart enough to get it, will realize that he is speaking to them, while throwing off the lesser dogs from the scent so he won't have to waste his time arguing with them. He lives in his own world. For as long as he is correct, then he has won.
He is very comfortable with Adam Back because he views him as an intellectual peer.
It isn't about real world results for him, although he doesn't rationalize it that way. In his mind, it probably plays something like, "by being the most correct, we will attain the best outcome".