What was the result of that call to Apple? Also I am very interested in the Office saga, two people using one copy on two computers, I expect you will need to purchase a family license in that usage case.
I have found the configuring Word will vary from person to person, depending on their working conditions. For example, while "smart Quote" marks look good on screen and on printed pages, the will cause trouble when you send a Word file to some print houses - somehow their printing software can't handle the way Word codes those quotation marks.
So I got in the habit of turning that option off, while most people leave it on.
BTW, your pictures were very good, but the lighting made the laptop look much lighter than I think it actually is.
If you can, please take a frontal picture showing the whole screen, with a Word file open.