Hey Tom, it's good to see you here again. 
I highly doubt the issue is related to playing the games on Windows before.
It's very likely a "Catalina" problem. Despite not using my old mac mini for ages, I've seen several complaints around the web (and SI forums) about this particular macOS version.
By the way, in order to find the "Application Support" folder, this was the regular way I was aware of:
Open the "Go to Folder" menu
Enter the path of the Application Support folder
Copy the following path and paste it into the "Go to Folder" input field.
~/Library/Application Support
Finally click "Go" to go to the folder.
No idea if it still applies to Catalina.

I highly doubt the issue is related to playing the games on Windows before.
It's very likely a "Catalina" problem. Despite not using my old mac mini for ages, I've seen several complaints around the web (and SI forums) about this particular macOS version.
By the way, in order to find the "Application Support" folder, this was the regular way I was aware of:
Open the "Go to Folder" menu
Enter the path of the Application Support folder
Copy the following path and paste it into the "Go to Folder" input field.
~/Library/Application Support
Finally click "Go" to go to the folder.
No idea if it still applies to Catalina.
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