Originally Posted by itimpi
I have been wondering if there is any possibilty of getting books added into iTunes from Calibre even when the device is not plugged so that iTunes simply syncs the books next time it is plugged in. This would allow me to get books added into iTunes as I work on them rather than having to remember what ones I wanted the next time I plug in my iPad.
Possible, but tricky as there could be interactions with other device drivers, for example if iTunes is running but you plug in a Kindle - who wins?
Please create an enhancement request. I need to make sure that things are relatively bug-free with the existing feature set before adding new features.
In the meantime, you could create a custom column 'Add to iPad' that would allow you to keep track of books headed for iTunes.