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@Hitch
It sounds like you've done a great job of training authors to use Word correctly. Bravo! I agree entirely that much of the trouble with Word output originates behind the keyboard; e.g., garbage in, garbage out. I also agree that it is entirely possible to write documents that generate reasonable markup in Word (and have proper TOC-generation information). This is less true the more complex your document, but for fiction, I definitely believe that 30 minutes of hands-on training can solve 90% of the issues users see.
Many of the authors we see who have the most trouble with their books are first-timers or very non-technical people. I believe that the interface of Word encourages them to use itself wrongly. It encourages users to do one-off styling instead of using the semantic tags like headers and whatnot that can generate useful metadata and be styled at a later time. It seems to me that Word's interface was originally designed for creating print documents and has not significantly changed since we've moved to a much more digital world. While it is possible to use Word in a way that doesn't cause problems when converted, I don't think most computer users do it that way by default.
I am intrigued by your suggestion that books can be easily fixed by macros. I personally no longer write in Word so I can't really suggest any good ones. I don't think most writers are competent enough to create such a macro. But I do have some interest in getting writers to use document cleaning macros provided by others if it helps. Have you shared any of yours or would you be willing to do so?
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