Actually it would. IIRC, the job class used for "Send to Device" are DeviceJob instances, which run one at a time. Choosing "Send to Device" with 50 books twice queues up the first 50 to run one at a time and then the second 50 behind the first, all to run one job at a time.
Changing this would require some pretty hefty reworking, and I'm not sure it would be a good idea or even something I'd be willing to implement anyway - there's a very good reason (the potential for corruption or missed updates) only one DeviceJob can run at any time!
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