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Most likely the issue here is with the paths.cfg file. It probably has an invalid path set.
You'll need to find and delete that (a reinstall will not automatically do this) and then things should work right again.
On a PC, this is typically found in the AppData folder, which is a hidden folder.
Something like AppData\Roaming\Out of the Park Developments\OOTP Baseball 27\config
If you go to the Windows search function and type %appdata% that should open the app data folder, and then you can navigate to the OOTP specific sub-folders and delete the paths.cfg from there.
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