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I can't help with the first issue, and can't read the diagnostics of the second. But I do know that the only time I've been able to connect to any of my iPads from Calibre with the IOS plug-in and the book program called "Marvin".
Even after installed, you have to open Marvin and while in the main menu, click the lower left corner and click "Get Books". Then Calibre will find the Ipad and show the "Marvin" icon when it's connected.
I don't think that there's anything in Calibre that will see inside an iDevice's drive in order to write books.
Outside of Calibre, I use Filemanager to connect to my main drive, and transfer epub files to the Ipad that way. When I click on them in the File manager it then asks me what program I want to open them in.
And I can use IFunBox to write files directly to the file sharing space of what ever programs store their info there. Although those programs may or may not recognize the files once they're open. It's trial and error to find out.
Also, if using both the Marvin and IOS plug in and Calibre, I've found that Calibre can't recognize the iPad if two iDevices are plugged into the computer at the same time.
Maybe this will help in some way.
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