Getting there slowly, one game at a time.
This is my little Wine/Lutris shelf right now, and everything you see here works.
Code of Honor 2: Conspiracy Island from disk works.
Conflict: Desert Storm 2 from disk works.
Delta Force: Black Hawk Down from disk works.
Dungeon Keeper Gold from GOG works, and I also installed KeeperFX.
Of Orcs and Men from disk works.
StarCraft from disk works.
StarCraft with cnc-ddraw works.
Epic Games Store works in Wine.
TextAloud 3 works in Wine.
Winamp works in Wine.
I have even live streamed most of them for about an hour each just to prove they are not only launching, but actually playable. The only one I have not streamed this time around is Dungeon Keeper, because I just installed it again, but I do have an old stream from the last time I played it.
It has not all been plug and play. Some of the old games have needed the usual Linux/Wine fighting: DXVK off, MangoHud off, old resolution handling, Wine virtual desktop, sound fixes, old installers, broken online registration junk, dead services, and all the other classic old PC game nonsense. But that is also kind of the fun part for me. I grew up with PC games on disk, and I like getting them running again instead of just letting them sit on a shelf doing nothing.
My plan is to slowly build up a proper old-game setup on Linux with as many of the games I played through the years as I can get working. I also want to install all the physical disk games I still own. If I fall over more old PC games at a price I actually want to pay, I may pick them up too.
I am not trying to make the cleanest or most modern setup. I am trying to rebuild my own old PC gaming history, but running on Linux.
One game at a time.