After some time now I do believe I understand where the issue lies.
Windows doesn't know what to do when a monitor plugged in through displayport wakes up, I'm unsure if it's the same with hdmi but mainly DP is the issue.
Since the power flowing from a sleeping monitor connected through DP cable is so much lower than older vga/dvi, windows completely forgets it exists when it wakes up. Then windows in its infinite wisdom panics when it shows up again, blames you and drops all the balls.
The "solution" that worked for me was to change a specific setting inside my monitor.
Setting > Power Button > Standby
This makes the monitor enter a slightly quicker wake up mode, which continually draws a tiny bit more power, enough so that the pc and windows can still detect it even when everything is off.
Ultimately this is more of a quickfix than a solution, windows freaking out should not be happening in the first place