That sounds like the classic example of a decorative feature that someone thought, "oh that sounds easy, add it to someone's sprint." But of course turns out to be mind numbingly complex.
I got the impression the problem in the comment above was too many extensions rather than too few. For example, you have use .docm etc rather than .docx if your document contains macros otherwise Word will refuse to open it (this is a security feature to prevent document viruses). But it sounds like there are many others.