Games, especially in the 90s (and some early 2000s) did a ton of API abuse so they are among the harder types of software to keep running. Still, most do work o

Games, especially in the 90s (and some early 2000s) did a ton of API abuse so they are among the harder types of software to keep running. Still, most do work out of the box and with 3rd party compatibility shims like dgVoodoo (for the older ones) and DXVK (for the more recent ones) stuff tend to work since the breakage is still very minimal. More regular applications tend to be much easier to get working though. E.g. something like Delphi 2 or C++ Builder 1 work out of the box just fine. The biggest issue with older software is that they sometimes had 16bit installers who do not work with 64bit Windows. Windows comes with some updated stubs for some popular installers and it is possible to manually fiddle with some of the unsupported ones to run the 32bit engine directly, though something like odtvdm/winevdm that emulates 16bit code on 64bit would also work. But in general you can get things working, depending on how well the application was written. In some cases (games, 16bit installers) you do need workarounds as they wont work out of the box, but even those workarounds are based on the 99.9% of the rest of the system preserving backwards compatibility.