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i see no sense in keeping duplicates of the original, i.e. with DRM, versions in the calibre library as they are stored for you forever ( or until Amazon goes bust) in the Amazon cloud. you can delete from/reload to reader as often as you like, in 60secs or less over wifi. So why not just put a single DRM stripped copy into calibre, that will work with every Kindle you have.
Also, once you've read Alf & set things up, DRM is removed automatically as you add each book to calibre - you'd have to keep disabling the plug in in order to add the original complete with DRM.
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