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@Bookripper,
I don't quite understand your approach, and I am afraid you are trying to use a reader, or at least Odyssey, for what it is no made for.
Apparently, you would like to sort and structure your documents according to criteria that are not consistent: in your example, you segregate "Horror" and "Novels" (!), but you also classify "Essays" in your overall "Novels" category. This hierarchical structure prevents you from managing documents that would belong to several categories (e.g. historical horror novels...), or Stephen King from having written an essay on modern horror literature.
So why don't you just manage labels in Calibre, which allows to manage absolutely anything in terms of information, forget about the tree-structure, and just use Odyssey with the four unquestionable available information: title, author, file name and file size ?
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