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Sorry for the delay responding to this.
I use a Mac, so I have some familiarity with this. OOTP has an option in the main menu to open the saved games folder, which I believe is set to the proper path in the Mac App Store version (as opposed to using the Mac version we sell).
Are you trying to keep your saved games and other OOTP folders on an external hard drive? It seems that it would be simpler to keep them on your Mac's local hard drive.
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