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Update, unfortunately the Calibre developer is not interested in in retrofitting the iTunes functionality moving forward.
So for me the best solution moving forward is Calibre 3.8 (with DeDRM plugin) and iTunes 12.6.3.6 with sync to my iPad/iPhone. This enables auto-removal of any *RM, auto-conversion to EPUB as required, ability to download/update meta data, add genre categorisation and books series (utilised in i Books) as required and sync with iTunes book files.
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