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To second theduck's post - use connect as a wireless device. Once connected, in calibre select all the books you want to send then press send to device. The is no problem sending hundreds of books in one go; I do it frequently as part of testing the app. You can also bulk delete books from your device while connected.
Enough people have asked for bulk (queued) downloads when connected to the content server that I am looking at how this could be done. The biggest problem is managing the queue. How do we show progress without blocking the app? Can the queue be edited before downloading has started? After downloading has started? How does the user pick which format to download, or is picking the format even possible? What happens if the connection is broken? What happens if the device goes to sleep or if CC is stopped? If we do anything then it must "just work", and I don't yet know how to do that.
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