For games, the PC Gaming Wiki is a treasure trove of "how do I get game X running on modern machines". Usually the culprit is either an ancient version of DirectX for 1990s titles, or DRM for the 2000s. And usually there's a crack/patch for the DRM, and for DirectX you can use tools like dgVoodoo.
If I'm going to have to tinker with stuff in order to get things to work, I'm just gonna use Linux. The whole point of Windows is it runs people's software with minimum fuss, if things have degenerated to the point it can't even do that anymore then there is no point in ever using this thing.
