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Well, my library was built pretty gradually, and I only have around 200 books, so I don't think the process was as difficult for me as for somebody who started out with a lot of books. So far, though, I put all of my books on all three of my readers, using calibre exclusively. When I add a book to calibre, I replace all of the tags with my own tags -- I have 10 or 11, I think -- and make sure that the series is correct. That takes care of the Sony because it manages collections based on my tags and series.
For the Kindle, every time I add a book to it (using calibre), I open it on the Kindle and add it to one of my 10 collections on there. If you view by Collection, you don't have any "stray" books showing as long as they belong to as least one collection. That makes my home page very tidy.
On the Jetbook, I usually just put the SD card in my computer and send the books to "file" using calibre. For a while I had a more complicated folder stucture set up on there, but decided I didn't want that.
I agree that I wouldn't want all of my books on my reader without any organization, but most devices now support some sort of organization, and I like making full use of it. For instance, if I didn't keep an "unread" category and a "reading now" category, I think I'd spend half my time poking around in there trying to remember what I was doing last!
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