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Coming late to this thread but the advice about heading styles is spot on. In my experience, the biggest mistake people make when creating EPUBs from Word is not using proper styles — they'll manually bold and enlarge text instead of using Heading 1/Heading 2. That single habit change gets you a proper table of contents and chapter breaks after Calibre conversion without any extra work. And for cleaning things up afterward, Sigil's live preview plus regex find/replace is the most efficient workflow I've found. Makes CSS edits much less daunting than working blind.
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