@Cannoli No clue what your doing wrong as it does work on other peoples systems including my own (before I updated it)
Winebottler, who knows whats wrong I hear it works but as it only provides a single wine version I avoid it plus doesn't offer winetricks but its own implementation that's outdated.
@baumaffe The current uploaded version of "PKHeX for mac" won't function on Catalina but it could if it used "Unofficial Wineskin" along with WS11WineCX19.0.1 it currently needs SIP to be disabled (wine32on64 needs to make changes to LDT and that's blocked for unsigned code meaning SIP needs to be off or donate to the developer so they can Sign the Engine)
Here is a screenshot of me running PKHeX using "Unofficial Wineskin" on macOS Catalina, already updated the app to the latest version but didn't bother swapping out the EXE's embedded icon