I'm not 100% sure I found my issue, but I certainly found something not good. My timing puck has been taking in oil!!
My theory: oil pressure rises, pushing oil through the shaft bearings of the timing puck. As oil saturates the internal timing wheels, it begins to start missing counts. The higher the revs, the further oil is tracked up the timing wheels, resulting in more and more missed counts. Of course in the AEM software it doesn't seem to indicate any timing errors, but that is likely because it's still reading the crank count inside the puck and attempting to correct itself
Fuck