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What theducks said. Down with slushboxes.
As for calibre, I got a little lost in what you're trying to do there. Hopefully the following will help you some; if not, rant in my general direction and I'll try to be less confusing. Mind you, this is from the point of view of a person who is using a Sony 505 and a mouse with multiple buttons, so your mileage may vary.
Import your books into calibre. You'll find a button for this.
Use the setup wizard to make sure your proper target device is selected.
Pick the books you want to transfer, select them, right-click, and click "send to device:.
They should be where you sent them.
If this doesn't work, either I haven't explained myself very well, or I don't know jack about iAnything. Or both.
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