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One other thing to consider is if you are going to be loading a whole lot of books onto his Kindle for him, it's maybe worth doing it in small batches and not dumping 100 books straight on there.
If you do it in batches and let the Kindle index those books, check there's no problem and then load on your next batch, index, check and so on. Just in case you load them all on and one book has some kind of issue that causes the indexing to get stuck.
You can check the books are indexed ok by searching for a non-existent term like 'xywqr' and on the results page it tells you if any books are still to be indexed. If it gets stuck on one book, there's a problem with that particular book.
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