He runs a company that provides advanced flight combat training. This actually makes some sense.

I mean, I've known people who owned ATF-licensed automatic weapons. They're scarce because no new licenses have been issued since the '86 ban, but prices for grandfathered weapons tend to run in the order of tens of thousands of dollars, depending on what you want and who's selling.

If you're looking for conspiracy theories, looking past the ownership of large numbers of military jets, to the handful of rich-enthusiast-grade small arms, seems like a weird flex.

Right? How does one "contractor" obtain so much power?

You are aware that the vast majority of defense articles employed by the military are not manufactured by the military right? Lots of companies have such licenses. The article even lists his competitors in this particular space.