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I found the solution to part #2 of my problem (making the Kindle recognize my "hand-made" TOC as such) by chance while browsing a completely unrelated thread (seriously, does this only happen to me?).
But the reason I was asking whether Calibre has a sort of "add 'Chapter' to all entries" function hidden somewhere was precisely to avoid the manual tagging of all chapters - whether by adding anchors or titles.
But I'll try Sigil anyway. Even though I'm not gonna make epubs, it's bound to come in handy.
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