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I think part of the problem is the workflow. Going from Word to Calibre then to Sigil will just introduce complications.
If you are diligent in the use of Styles in the Word doc, and use Word to generate the Table of Contents, you can end up with decent code.
Save it as a filtered web page.
Bring it into Sigil. Create a stylesheet that has just the styles that you used.
Delete all of the internal style information in the document - everything contained in the style element in the header.
Now the stylesheet will control all the styling.
Bob
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