So to try and help simplify things I elimated the outer loop and all of the switches except for the two O31 switches that make up the reversing loop. I am only using one lockon now so that removes the power being routed from the outer loop to the inner loop.
I was easily able to replicate the issue three times in a row so no change. I tried spacing the tracks and no change. I wired up the one switch location with the issue to auxillary power. So the switch in the video has its own dedicated 50 watt power supply nothing else is connected to it to draw power. So the power momentarily still goes out to the switch but the track power maintains. The switch does not fully engage on the first pass but does on the second. There is improvement but still no resolution.