I'll answer as best I can then let the experts take over.
You don't "sync" with your kindle.
The 'transfer' button on Calibre is that square thing with the three blue 'knobs' on top.
There should be an arrow, click on the arrow, and choose "email to xxx@xxx"
If that option doesn't appear, its not set up to go.
Or....you can use your usb cord and transfer books that way.
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