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I see. I'd argue that queued device sends should just be sent to the first device connected, that would take care of your points 2 and 3. I'd argue against including deletion, since, as you mentioned, you never know the state of the device when it gets connected (I'm thinking manipulation outside Calibre). In the end, that's all rather academic, since, as I mentioned before, not only are you not interested in such features, but neither am I (apart from the point where I thought "Hey, that would be cool!".).
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