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The ability to easily search anything in my whole library if I want to, when I want to, would be my reason for wanting them all on my Kindle 2.
I've recently replaced my original Kindle due to not previously noticed sun-fade problems, so I don't yet have all my ebooks on it, but my previous one had over 500, and my Calibre library now has over 800. I intend to put them on gradually, and hope the huge number of books doesn't cause it to run slowly. I noticed when swapping that the newer (emptier) Kindle responds much faster than my old (fuller) one did.
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