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I wouldn't put 50 at a time on a Kindle. More like 10, maximum, until it has a chance to index. Plugged in is a good idea, though. There's no rush to get the whole library on there, really. Just enough for what you want to read soon, then gradually add books until whatever you want is on there.
Personally, I see no need to put everything on my Kindle at one time. It isn't like I can't move things over from the pc any time I want.
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