The only thing I can think of is that the displays are completely disconnected, and that upon waking, they initialize in a different order causing a different order when enumerating. When you start your laptop, the wait on bios post is probably long enough all windows to be fully connected and ready by the time you hit windows.
- You could try sleeping monitors immediately to start day, then waking them, then see if monitors keep the apps on correct displays as the day progresses.
Just for fun, trying disabling fast boot in bios and fast startup in windows. Probably won't make a difference.