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Until you have downloaded the book, it will not show as being on the device. Which makes sense since until you download it, it is not on the device.
As for the other book, are you reading a copy that was synced to your Kobo or are you reading a copy that was transferred over USB? If you match the copy synced from Kobo to the copy in calibre, the reading status, for me, does show up. If you sent a copy to your Kobo over USB does the On device column show 2 (or more) copies.
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