This question is about best practices, and not necessarily my how I manage my current setup.
I have these two scenarios, macOS Mojave with KeepassXC, and Windows 7 + Android 8.0.0 with SafeInCloud. The first is a work machine owned by my employer, while the second is my personal machine and phone.
Right now, I have to remember five different passwords, all of which are machine generated. Because of this, I am always hesitant to update my passwords, it has been well over a year since my last update, and I, personally, am wanting to update. I store my work OS+PWM passwords in my personal PWM, so that if I forget my credentials (which happens) it doesn't become an issue for my employer. I do not, however, store my personal OS+PWM passwords in my work PWM.
To reduce the number of passwords that I need to commit to memory, and thus feel more comfortable with password updates, I want to share my OS passwords with their corresponding PWM master passwords. This would give me two machine generated passwords to remember instead of five.
Moreover, if my employer needs access to my work machine for any reason, I don't want to hinder their access by requiring them to juggle this problem too.
What are the best practices for sharing an OS password with the Password Manager password?