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Troubleshoot App Issues: Logging?

I have been trying to run some older emulation software and the apps crash on MacOS. I realize that I am tempting the IT Gods by running an M1 Mac to simulate Windows emulating a Commodore 64 but tech marches on and I refuse to march with it. What I am wondering is if there are logs that I can turn on so that I can maybe troubleshoot where the issue is and what I might be able to tweak to get it running.

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