Mmmmm.... this could work but not without first sending/synching email accounts. Seems to me as soon as you check the box and hit apply, it goes into auto synch mode.... until it is set up.
SInce I have 2 compeltely separate Outlook environments (Work and Home) I have no idea how it will handle the email synching. For calendar's I know they are in separate locations/folders so work well.
But I may have to just try it.
Problem is... unchecking may not display, but does it still synch anyway.
There is also security issues of my work email becoming part of my home icloud account.
One thing Windows and Apple have never understood is how to keep these two separate.