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From my testing it appears that Amazon is being very frugal about delivering these files for sideloaded books. I downloaded a book using Download & Transfer and sideloaded it to my Oasis. Shortly afterwards the X-ray and Wordwise files appeared.
I removed the book and sideloaded the same file again. This time no extra files appeared. I was only able to trigger delivery of those files by first making another Download & Transfer request for the same book.
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