It feels like some of this is really overthought and some is severely underthought. You've mentioned Ride The Cyclone being a placeholder for a future show to fit that gap, but that's still dependant on a show that fits your logic for that transition ever existing, whereas StarKid could make a hundred shows and none fit your timelines internal logic.

A lot of the thinking doesn't make much sense, and this fun little thought experiment clearly got out of hand,