Also I remember back from my gaming days that some then-old (now older) games required specific hacks or workarounds to run on "real" then-modern Windows, some

Also I remember back from my gaming days that some then-old (now older) games required specific hacks or workarounds to run on "real" then-modern Windows, some possibly incompatible. Whereas Wine could be made to have tailored instances per game (which I think PlayOnLinux, Crossover, Proton... are doing), giving the best experience for each game. IIRC there are even some games that can now only be run on Windows by running them via Wine on Windows.