One of the biggest things holding me back from jumping definitively on Linux is possibly getting rid of the apps/games i'm comfortable with and know well. How do you exaclty use Wine/Proton? You install it, launch the app with it and pray it works? Are there ways to know what is not working and possibly try to fix them googling or reading the documentation?
Probably not the answer you want to hear, but I just use steam and proton db. If something doesn't work or I can't fix it, it's the cost of freedom and I do without.
Bonus points you can be a moralistic douche when your friends give you a hard time. (You'll have to do without friends too.)