If you want to get old 16-bit programs (like Civilization 2) working on windows, try winevdm.

https://github.com/otya128/winevdm

I managed to get Areena 4 and Civ 2 working using that.

I think it’s pretty dumb that windows doesn’t include a way to handle 16bit software on 64bit OSes. They can run 16bit on 32bit systems and 32bit on 64bit systems, so what’s the problem with 16bit on 64bit systems??

I’ve been using dosbox to run 16bit software. I found a version with win3.11 preinstalled to make accessing the woftware easier. (You can of course just install windows onto dosbox yourself, but I didn’t feel like putting in that much effort.)