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My advice would be to install just calibre and the DeDRM plugin.
Then import your ebooks, checking that the DRM is getting stripped. Metadata will be read from the books, but might need some adjustments.
That's really all you need to do to start with. Get comfortable with importing books, and sending books to your device, without the use of any extra plugins.
Then once you're comfortable, you might find that you do want to add some extra features through plugins and/or by adding custom columns to your database. But any of that can be done later - it doesn't need to be done when you first start using calibre.
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