Please Please Please make it so that subitems populate to the calendar view of my work.
Subitems do populate to the calendar view of My Work. Just tested it now.
I would go check your settings in the “Customize” menu of My Work and make sure the date column has been chosen for subitems of the board you want the subitems to be showing in the calendar view. Also wouldn’t hurt to make sure the board itself is visible as well while you are there.
Hope this helps you out.