averageguy2022: Wow, theres a lot of knowledge and support here and it is very appreciated. neumi5694, you're right it was often a challenge to get these games working right and chasing after more horsepower.
Many problems can be solved with virtual graphics card adapters like dgVoodoo, but not all.
SW EP1 Racer for example would turn white after completing round 1, some fans wrote a dll that fixed that. Microsoft allowed some DirectX hacking which has been forbidden since so whatever the original dll did, was not allowed anymore.
Other games - like the original Croc Legend of the Gobbos - which did make use of specific hardware, would only run with limited functionality. Croc used AWE to play background sounds, this way saving CPU power. After direct sound card access was cut off, that would not work anymore (later a version of the games was released that only used DirectSound).
In many other games we don't get surround sound anymore, since they also are using APIs for that, which require direct sound card access.
In that case, virtual sound card drivers like IndirectSound or SoftOpenAL help. They may not yet support all EAX effects, but at least they give us our surround sound back.
In Telltales case it's about direct input, which was updated with Windows 10. Telltale games would require an old version of it. The solution was simple: Get a old dll and put it into the game directory. But Telltale never bothered to update their games, so we had lots of crash reports when people were using a XBox360 gamepad.
TL;DR
Most problems are not connected to the Windows version in use, but based on the use of old APIs that are not supported anymore or the direct access to specific hardware.
Often the games put changeable game data into the games directory and therefore require Admin rights when they get installed into a directory the standard user should not mess with (like c:\Program Files, only Admins should write there).
In very few cases the game code is shit and uses hard coded or - even worse - language dependent directories. That can be a problem if the Windows system is installed differently than in 1995. These days user directory and OS can be located on any drive, not just c:\