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The system I finally worked out was to create the collection name on the device and then move all the books in that collection over to the Kindle using Calibre. If you use the Calibre column customization or Collection tools to help organize your collections it helps a lot. You can limit your Calibre screen to just those books, select them all, and then mass move the books.
Then I'd go into the Collection and choose "Add/Remove to the Collection.". Sort the books by most recent first and all the books you want should be in the first pages.
There is a wonky bug here and a good number of the time when you choose add to the collection you (or at least I did) get a blank screen. Back out of that blank screen and repeat - choose add/remove books to collection again and this time it should work. I sent off an email to Amazon about that bug but never heard anything back.
Anyway, with the books sorted by most recent first it is much easier at least to find them without having to go through all the pages of all your books. I can't tell you how many to do at once because I think my largest collections only have about 25 books in them. 25 seemed to go fine.
I know it is frustrating, I'm really hoping that Calibre plug-in gets an update.
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