I regularly add ebooks to my PRS-505 without any specific ebook software; just copy & paste the files into the right folder on the extra drive. (Right now, I don't have Calibre or the Sony Library installed on my main computer; I'm still sorting out weird Vista issues.)
However, with Calibre, you can tag books in order to group them, and fix the metadata. While those aren't always necessary, sometimes they're very useful. But you don't need it to transfer ready-to-read books to the reader.
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