I made a point of putting all our books (DH and mine) into cloud collections right from the start. Personal document ebooks and Amazon ebooks. It's a process that's automatic now so I don't have to wade through pages of books to get to I want. I agree it's a pain to start with if you have a lot of books, but it pays dividends now.
I don't need a jailbreak to manage this, or a Calibre plugboard, I simply put a new kindle book into the right collection, then match the collection when I load the books into Calibre. Between us DH and I have 63 collections.
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