The Wrights had some considerable (at least for the time) experience on biplane gliders and not by chance. They practiced on gliders with the same control setup (cradle, wing warping, etc) as they used on the 03 Flyer on purpose and by the time they flew the powered airplane had maybe an hour or two of total time. None of it was dual, obviosly, so I guess they could log it all as PIC, in 15 second increments.
I believe the last of the brothers last flight at the controls of an aircraft was a super connie in the late 1940s-1950s, but don't quote me, I dont have the books handy.
I wonder if any of the PC based simulator crowd would like to try a Wright Flyer simulator with the cradle on a simulated wing center section, the prop noise behind you, the wind blowing, the whole thing on a 6 DOF motion base and a projected computer generated visual system. The visual wouldn't take much computing power to generate just sand and sky and the odd gull. Consumables would include a bag of sand or two to be blown in the students face.