The waters of the Air Warriors ocean are cold and bleak for the type B personality. Either that or somebody's been putting too much vodka in the AW Kool-aid lately.
He obviously has a fair amount of flight time in a structured environment already. Just because he doesn't desperately need to get into the Navy at all costs doesn't mean he's going to half ass things. As far as being an officer, and asking questions that clearly aren't those that an officer would ask I would venture to say that a vast majority of regular joes that go into OCS have no clue about the culture, noblesse oblige, and the deep sense of pride comes with leading the nations finest into battle. Why would he NOT ask these questions? He wants SA. Just answer the questions, and if the answers fit properly into his go/no-go criteria, then I'm sure he'll get the properly adjusted warrior ethos in the training pipeline.
My suggestion to OP...Read some books off the Commandant's Reading List and see if they speak to you. If they do, then it might be a correct fit. If not at all, then have fun sweating your ass off trying to prepare for your interview with the regionals.
The questions were pretty much answered. For those of us who have been there done that, there's a reason we come across as we do. That or we just have way to much time on our hands.