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For the TOC you have to tag the chapters wth the chapter style. You can do that by highlighting the chaptter text and pressing the chapter button or selecting the the chapter style.
Inserting page break is the corect way to do it I don't know why it is not working.
If you wish send me a PM with the code sample. I'm on vacation so I won't be able to look at anything for a few days.
Also calibre has the option of auto page break when creating chapters I choose to turn that off and allow the author to determine when they want a page break
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