My setup is probably not typical, so I don't suggest using it as a guide, but some parts might be useful.
I have all my books in Calibre in ePub format, but on my Glo I have some of them in KePub format synced from my Kobo account and others in ePub format sideloaded from Calibre. Calibre matches the kePub books on the Glo with the ePub version in Calibre, and so I can use the KoboUtilities plugin to change the covers and other metadata on the KePub books too.
I use KoboUtilities to add ISBN, publisher and date which show up in the book details page on the Glo.
I also use KoboUtilities to set the series at the same time I set the ISBN etc. rather than set it automatically, because I have some series indicies set to non-numeric values (such as 3,4,5 for an ombibus containing books 3, 4 and 5 of the series) by manually editing the device database and I don't want them to be overridden by Calibre which is unfortunately limited to numeric values.
I have the KoboTouch driver set to Upload covers for books and Keep cover aspect ratio, which generally results in much better looking cover images and thumbnails than allowing the device to generate them from the first page of the book.
In order to reduce the length of the filenames used by calibre when sending the book to the device (especially for books with multiple authors) I use this save template (e.g. the book 'Roseanna' by Maj Sjöwall and Per Wahlöö is saved as 'S/Sjowall, Roseanna'):
Code:
{author_sort[0]}/{author_sort:list_item(0,\,)}, {title}
I use this metadata plugboard to make the device show books with multiple authors properly (The device treats 'and' as a special word in author names so it sorts multiple authors correctly, e.g. 'Maj Sjöwall and Per Wahlöö' is sorted alphabetically as if it had been written 'Sjöwall, Maj and Wahlöö, Per'.):
Code:
any format:KOBOTOUCH = ([{authors:'re(re($, '(.*) & ', '\1 and '), ' & ', ', ')'}] -> authors)