I was lucky that when I moved to Linux some months ago I got used to install my games from Lutris and Steam, which seems to solve most problems and only maybe 1 game of the 15 or so I tried so far wouldn'twork no matter what.

That said, I and to figure out how to do diagnostics and use Winetricks and my little doc of Tips & Trick cover 5 games (out of about 15) so those are the ones that would work only after tweaking.

I still have weird situations like The Sims 3 from Steam not working but the pirate version I tried working flawlessly on first try (so now I know how to install pirated games with Lutris) which is maybe not the kind of thing the publishers would want people to know, but more often than not things just work.

All this to say that it's way better now than before if you use the kind of tools that wrap Wine (or in the case of Steam, Proton which is a derivative of Wine) with install scripts that will do the necessary game-speciric tweaks for you, but even then you'll need to learn how to diagnose problems and do the tweaks yourself if you want a higher that 60% or so rate of success or if you want to hoist the Skull & Bones and sail the high seas from your Linux Galleon.