Automator or script to keep outlines synced?
 

I'm using iTunes to move outlines onto and off my iPad. It works fine, but every morning I need to manually select the outlines on my laptop, drag them into the iTunes OO documents window, and at the end of the day, drag them back.

Is there an Automator routine or Script that could do this?

Not sure. Ask robthrew who has no family but lives with AppleScript instead. However, Omni says they are working on iCloud sync for all of their text based apps, like outliner.