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Okay, going to troubleshooting and clicking on the "open file 'paths.cfg'" leads me to users/user/library/application support/Out of the Park Developments/OOTP Baseball 16/config. My save game file path is exactly the same except /saved_games at the end instead of /config.
Here's screencaps of my /config folder, and my /saved_games folder. As you can see, there are two "saved games inside the saves folder, the first is the backup I manually placed there (which doesn't show up when I try to load inside OOTP) with all the subfolders and files inside, the second is what's created when I "successfully" restore a backup as I outlined in post #6 above, which as you can see results in a totally empty save folder.
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