Vintage gaming community.
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The sheer amount of finagling required to get older games working on modern Windows is a big reason why projects like ExoDOS and ExoWin9x are so important for game preservation.
Getting these games to play from their original media is only going to get harder over time; eventually, playing archived/preserved digital versions will be the only way to experience them.
@noumenon it depends on how old! Are you talking Windows 95 old or Dos old? Either way, step 1 I suggest is to start from Linux. Step 2 depends on your answer to the above :)
Its not exactly easy on linux either at least for average users like me, unless you are lucky to find a lutris script specifically for the CD install.
at least in my experience.
@A_Random_Idiot well for example Alpha Centauri and even Civ 2 were really easy for me. I used wine without any wrappers, I simply set an older Windows compatibility version in winecfg. StarCraft also worked easily though I wasn't able to set it to full screen properly on Wayland and had to re-login into Xorg for it. Let's see if OP provides us with more details
last time I tried it was Simcity 4, and I couldnt get it to install right.
But I'm not an IT/SysAdmin professional. I'm just a random idiot, so my capabilities with linux.. while improving over the years, are still far from useful in most circumstances.
Bottles, Lutris, Heroicgameslauncher, Steam. Between those 4 you should be able to get atleast one of them to run an exe to install a game. I think Lutris like you said actually has a "Run install.exe" option if you can point it to the right spots.
Persinally im just a dummy myself and flail around in Linux until it works, I've found its much easier though if I can skip the install process and just point one of the above 4 directly at the games folder.