You can somewhat simplify Dr. Drib's step 2 by clicking on the Device button in calibre's main toolbar. That button shows up when you plug in your kindle and it disappears when you eject/unplug your kindle (eject is safer). When you click that button it shows you all of the books on your kindle, in particular the ones that aren't in your calibre library. There's a column on the left, In Library, which shows which books are in your calibre library; you may want to copy over any that aren't in your calibre library, but probably not the dictionary or kindle user manual.
You can click on the Library button to show the books that are in your calibre library and that has a corresponding On Device column for what's on your kindle.
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