WINE generally does old titles fine.
Proton generally (90% ish) does new titles fine.
Very very old titles may need older wine versions, due to odd, depreciated behaviors in ddraw and pals. (Diablo 1, being infamous)
All of these cases can be handled with things like Heroic game launcher, Lutris, and co.
I'd say you would be hard pressed to find a vintage windows game that cant be made to run with existing tools.
As for 'vintage linux builds', i'd say the main issue comes from 'version pedantry'.
'No, I want THIS SPECIFIC ia32 library! NO, THE SAME LIBRARY FROM ANOTHER DISTRO IS FORBIDDEN! I dont care about it having the same functions and calling ordinals, the magic strings dont match!'
Much of the problem could be solved with shim libraries and some env variables to define the version to lie about, imo.
Many distros already give shim libraries for older versions to avoid dependency hell, but the version pedantry persists.