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Thank you very much for the screenshots, because they explained the first point
1a. Both bookmarks are 'Where you stopped' auto bookmarks. Those are a special kind, automatic and those are never sent to Calibre. By special I mean: these move all the time, while you read, they do not stay. Try making a bookmark manually on your own.
1b. Before sending JustRead check if the server is alive.If not, it does not send anything and waits for a next turn.
1c. No, JustRead does not remember a percentage or page number. It saves the exact place: the chapter file and the exact position inside it. The saved place doesn't depend on pages. From the next update the percentage is used only in two cases: when an update renamed the chapter file your place was in, or when you never opened the book in JustRead and Calibre's Progress is all there is.
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