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Note sure about your Kobo.
Answers to your kindle questions:
Yes, they can work with calibre.
A Paperwhite is e-ink like your kobo.
The Fire is a tablet with a kindle app. And is backlit not frontlit.
Note: reading on a fire is different from reading on an e-ink.
There is a kindle forum here for any other questions you may have.
I have a kobo, 2 e-ink kindles and a fire.
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