Annotation support (Kobo Utilities), series, and collections all work far better on the current Kobos than PW3. I only use my PW3 to buy Kindle ebooks. The Libra SW integration to Calibre is far better.
Don't trade in. Keep the Kindle as it's the best way to buy Amazon ebooks (download PC for that model) and read them on the Libra via Alf and Calibre.
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