Thanks for responding guys. Yeah Brundlefly, maybe I wasn't clear in my post. The scenario I wrote out was just a non functional example of how to reproduce the bug, not something I'm attempting to do.
In real world work, I am usually dealing with 200+ tracks and the people I work for expect every note/hit to be perfectly on time (with many instruments tracked with many mics). So I have to be editing extremely fast, which means even when editing a single guitar take (with palm mutes or defined strumming) made up of 3 mics and a DI, I'll be making 60+ cuts, nudges, slip fills (and auto cross fades when it used to work) a minute. With this kind of pressure/time expectations, this bug just completely destroys my ability to deliver.
ReginaldStJohn described a similar bug to the one I am experiencing if you want another example (although it seems a bit more functional than my problem).