If he were considering the military route, I'd consider 'boring' over 'sexy', transports over tactical. Airlines will fight over a guy 30 years old with a bunch of heavy multi-engine time. They'll hire an F-16 driver too but I'd think the C-17 driver with lots of long haul international experience is going to have the easier time. In either case, connections made in the military will likely pay off post - active duty.
That's a very good point, Curt...logically, multi-engine hauling experience kicks the airline training process into a faster track for sure. It also brings experience operating with a crew rather than independently and I suspect that's helpful, too.
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The most expensive tool is the one you buy "cheaply" and often...