I have done several clean installs of macOS Sierra and macOS High Sierra in order to give you the most accurate information possible. Regarding PKHeX, It's going on almost a year and I have yet to experience any depressive issues using WINE to run it. With that being said, I have been using WINE for quite some time. Nothing we do in this guide is permanent, although I encourage you to make a Time Machine backup of your system or at least backup your important data. WINE is a fickle thing it's not guaranteed to work (at all) but the success rate these days is impressive! So, don't get discouraged if things do not work the first time around.
This guide will hopefully clarify a few things regarding WINE and PKHeX running on MacOS as well as help anyone start from scratch with WINE.
