i think you will find that the Kindle 5 way controller works independently of what is in the toc and works even if the toc is mssing, because all it does is skip to the next header tag.
to see if Kindle thinks it has a TOC you need to go: book - menu - go to - then select the TOC option & it will them show you what it has.
I sort of gave up trying to understand when / how / if calibre builds TOC - I settled for convert to epub, then open + save in Sigil , then convet epub to mobi -which seems to consistently create a good one ( so long as H2 tags exist in the document )
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