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I believe that Calibre is using the <h1> and <h2> tags in the html file to create your end-of-mobi TOC, not your hyperlink TOC. However, I stand to be corrected as I'm not a mobi user.
The <h1> tags in the html file are automatically created from the Word 'Heading 1' styles and <h2> tags from 'Heading 2' etc.
I'm attaching a small sample Word doc containing 'Heading 1' and 'Heading 2' titles. I have not created any inline hyperlink TOC.
I then saved it as Webpage-filtered, imported to Calibre and did a zip-to-mobi conversion using the settings I listed above in post #2. As far as I can see, in Kindle-for-PC, the mobi is doing what you asked, i.e. a pagebreak for every H1 but not for H2s. The 2-level TOC also looks correct.
I've attached the mobi. Am I not understanding something fundamental?
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