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I don't know if the T1 will allow you to download DRM'ed books directly on the device yet. It is supposed to allow download of non-DRM'ed books. Hopefully file transfer sites like Dropbox will work.
If you only transfer the Kobo book to your reader (via a method like Adobe ADE, drag-and-drop, calibre, SD card, etc.), then it will only be on your reader. You will have to download the Kobo book to your Mac and then import it into the Reader for Mac software.
To do my testcase, I already had a copy of the Kobo book on my 950 that had been downloaded to my Mac and then transferred to my 950 via syncing with the old Reader Library software. I then imported the Kobo book EPUB file into the new Reader for Mac software. It was able to sync the Kobo book between my 950 and the new software.
I hope that my explanation is not too confusing! I think another way of saying it is that you have to have identical copies of the book in both the Reader for Mac software and on your ereader for it to sync properly. It won't recognize the books that are only on one or the other. You will have to load the Kobo book into the Reader for Mac software.
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