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Export from Calibre as an RTF if you don't have Wordprocessor source.
Make sure everything such as headings, styles and images are OK in the Wordproccessor (Word or LO Writer). Save in native format for later edits. Save AS in docx.
Import Docx to Calibre.
Make sure page format settings is Tablet.
Make an epub2.
Upload that to Smashwords, Google, Amazon KDP etc as desired.
I've had 100% success with that and no issues with TOC or images for years.
Though all our source texts are either our own LO Writer documents or Public Domain Mobi files (We don't upload those anywhere and usually convert direct to epub to read on a Kobo. Sometimes we export PD or Amazon mobi or AZW as RTF and edit to fix severe formatting issues for our own reading.
Only items to be in the System TOC should have a heading level.
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