@flipsat - not directly a solution to your problem but you might also want to consider using the Reading List plugin. What I and others do is instead of using send to device is just add books to a reading list associated with that device instead. Then when the device is next plugged in the books on the list will sync to that device. Or even while you have it connected you can queue them up and do a manual "sync" - it is less work for the calibre UI to not keep refreshing itself after you send each individual book when doing ad hoc sending.
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