I’ve had issues with various external displays over various MBP models forever, particularly waking from sleep. My current display had no problems at all with my previous 2014 15", but when that one died I replaced it with the first gen 16" and all those problems came back.
That said, I stumbled on a solution that’s been almost totally effective: I only ever wake from sleep with the TouchID button. I suspect (not very educated hunch) the problems with this newer model have something to do with timing of wake/power signals being sent before any other device data while waiting for the T2 to unblock.
Anyway, you might give it a try. I think I’ve had to re-plug all of 2-3 times in the last year (whereas failure rate waking from my external keyboard was close to daily before, and required a reboot at least a couple times a week).