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@crouton, perhaps you could share how you kept track of which books you had ‘read’ on the Kindle Keyboard? And are these books side-loaded, purchased from Amazon, or a mixture of both?
If you get them from Amazon (or have uploaded as personal documents) then reading position should sync to whatever they were when last synched, and all your annotations should be there as well.
If you side-loaded, then you’ll pretty much have to start from scratch (at least if not using calibre - I don’t use calibre enough to know what it can and cannot do in your situation).
Kindle Keyboard does not support cloud collections, or the notion of read vs. unread. There used to be a way to initialize cloud collections to what they were on an older device, but I don’t know if that’s still possible (I don’t see any option for it, at any rate).
Recent Kindles let you toggle Read/Unread status, and automatically set it to ‘Read’ if you get to the ‘end’ location of the book (as publisher defines it). But again, this only applies to books from Amazon and Personal Documents. You can mark anything as READ but if it doesn’t sync reading position to Amazon servers, it is only READ on that device.
When the READ feature first appeared, I did have to update this status for a number of books in my library, though most were already in the ‘proper’ state. Prior to this I had ‘Read previously’ and ‘To be read in the future’ collections to track this, but I no longer require these (a good thing, since Kindle does not perform well with collections of several hundred items in them).
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