We do know from the bicycle video that a second person wore the second watch at least some times. What if one watch was in the RV moving slowly while RY was out running or riding the bike or hitching rides, maybe leapfrogging the RV and hiding from Michael when it drove by? And which watch got uploaded was dependent on what happened?
Am I remembering correctly that Dustin had a bicycle on the RV? Otherwise there would be no reasonable way to bring a bike along without attaching it the RV when it wasn't being used. The bicycle theory certainly fails Occam's Razor, and does require Michael to be clueless, but it's seems merely unlikely not impossible. It also doesn't match the Asher incident.
I think hitching rides was probably done very sparingly (my guess is only during the RV breakdown) as it would be more risky to involve more people.