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I highlighted the ePubs in Calibre and dragged them to that window but they wouldn't drop in. I have no idea why. I have iTunes 10, I am trying to avoid 11 since I hear that it really, really sucks.
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Just wondering - are you trying to drag n drop from the Calibre database window?? I didn't think it would do that. Even if it does you wouldn't necessarily be getting the most current version if metadata/covers etc unless you "save to disk" first. If you right click on the title in Calibre you can select "open in folder" (or something like it) then drag from there to iTunes.
I upgraded to iTunes 11. It takes a little getting used to - and no, I haven't gotten used to it - but you can hit ctrl-s to get the side pane back. Then it is almost the same as 10...
Cheers!