The most common experience I have trying to run games through wine, lutris, bottles, and half the time on steam, is I click the run program button and nothing happens. Literally zero feedback. Some methods get a microsecond of loading cursor. Anything where a program has to alter or update a directory is maddening. Like I got touhou 7 running through steam pretty easily but no chance of figuring out how to apply the English patch.
The one that finally made me boot windows again was project diablo 2. I actually got bottles to run the installer over its internal folder for diablo 2 and ran it once a year ago, but trying to do it again with recent version, I just couldn't trick bottles into running it again.