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The Word/LibreOffice to Calibre pipeline that was mentioned earlier is really the sweet spot for non-technical people. The key thing I'd emphasize is teaching them to use heading styles consistently (Heading 1 for chapters, Heading 2 for sections) — that alone gets you a working table of contents and clean chapter breaks after conversion. For the final polish, Sigil is hard to beat. The live preview makes CSS tweaks much less intimidating than editing blind, and the find/replace with regex is invaluable for cleaning up the little formatting artifacts that Word tends to leave behind.
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