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Basic Calibre operation theory: There can only be ONE 'Master' Library
(if you
peek beneath the skirts, you will see the title name has a number in paren eg The Book(42). That links to the record
id in the DB. These belong ONLY to the pair in that Library. The same book, may get a different record id in another Library.
A 'Master" is the ONLY one that gets any changes:
Changes include: Metadata, adding/removing formats, EDITS
Different OS use different file timestamps, so TS resolution is out.
Different OS are CasE sensitive, so that tosses sand in the gears
I think you need to just use the Content server, Keeping ONE PC as the Host / Master. Do note that Kovid has added the ability of the Content server to manage some Library metadata.And it has user permission levels.