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PlexTraktSync
A python script that syncs the movies, shows and ratings between trakt and Plex (without needing a PlexPass or Trakt VIP subscription)
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Webtools NG might be able to do what you want, specifically the View State Copy feature. I haven't really messed with it so I'm not sure if it will do exactly what you're looking for.
My tentative plan is to use two instances of PlexTraktSync to have one directional sync from our shared Plex profile to our individual Trakt profiles (if we watch something together in Plex mark it as watched for each of us in Trakt) and then two more instances for one directional sync from our individual Trakt profiles to our individual Plex profiles.