Earlier quoted context omitted.
[[Citation Needed]]. Other than 16-bit software on 64-bit Windows, do you have an example?
A lot of games, Red Alert 2 off the top of my head. Never got it running even in compatibility mode and changing the bit depth.
However, I sympathize with the general funkiness of running old games. It's very difficult to play the original Diablo 2 through Wine unless you emulate a virtual desktop, which is frustrating to set up. If you're willing to give it another try, the Lutris script should handle almost everything needed to configure it right: https://lutris.net/games/command-conquer-red-alert-2/