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In my own case it's very much because I've been buying books for an awful lot of years, and from all sorts of different sources, many of which no longer exist (eg FictionWise, BooksOnBoard). Maintaining my ebook library in a single place (Calibre), and sideloading all my content means that I have a single central point where all my books are stored, and no worries about trying to remember where I bought each book from, or what devices I can load it onto. I can read all my books on all my devices.
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