Several months later (now) I've revisited this and have completely wiped all instances of Wine viaSegmentation fault: 11
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brew uninstall wine-stable
I've also ensured I installed GStreamer.framework. I even tried installing winetricks.
I've attempted to run the .exe from the command line with
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wine program.exe
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wine64 program.exe
(I've also ensured I have the correct directory location when using cli) as well as right-clicking in Finder and choosing "Open with.. wine-stable.app"
I've tried so many combinations of versions of Wine and continue getting the segmentation fault error. I've searched other non-wine forums and see that this may have to do with a memory error or translation error but cannot seem to make any progress.
I'm hoping to see if anyone might have any insight or alternative direction for troubleshooting.