I shouldn't think you should need to turn off auto-checkout. I keep it on. I don't know why sync isn't downloading it for you. What worries me is that you are seeing a hold option for a book you've already checked out, I don't think THAT should happen. Unless maybe your library has more than one copy to lend and there's no wait list.
Nor should downloading the book via ADE also have any negative effect on the sync, because I've done that as well.
Hope someone more experienced can help you!
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