@SampleAndy
(I am bringing your PM question online)
I don't use Kindle for PC, so I am no help there.
You might set up a (Calibre) Auto-Add folder and drop books there. This way, Calibre does not have to be running. It will pick up the books the next time it is 'Run'.
You might want to Set/Adjust Preferences: Adding Books: Auto Merge
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