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Have you tried editing the epub file? Through Calibre or Sigil?
Tools, then Fix all HTML files. You can try giving it a go. There might be some html files/tags that are improperly placed. In my experience, Sigil has a stricter editing tool. It will show you possible errors with the tags on every html file you're viewing.
Since you've said it's only happening with this particular book, then it might be the content of the book that Kindle is having a hard time reading.
Also, have you tried renaming the book? How about stripping all the metadata and just dragging it into your kindle folder? If it's not with the content, then maybe your kindle/account is confusing it with another title you have on your library/cloud.
I don't particularly like sideloading directly now because I'm a slave to whispersync. But I did so when I was still using a Kobo. I remember having to edit some ebooks in order for them to show/open properly back then.
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