Thanks a lot for your suggestions.
Am I right in understanding that 'send to Kindle' would make the books appear as 'personal documents', while sideloading them via Calibre would make them appear as books? Would they be backed up and synced to Amazon's cloud in both cases?
How about syncing between the Amazon Cloud and Calibre? Say I sideload a book from Calibre to the Kindle, read it on the kindle, and take some notes/highlight some passages. Is there an easy way to sync notes and highlight between Amazon and Calibre?
The main thing I don't like about Kindles is that managing collections is a huge pain, especially with the newer models, which need jailbreaking, whereas Kobo shelves can be created based on Calibre tags (or any other column) in a much more straightforward way.
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