I did the same, and when I switched I just switched to Linux rather than another Windows version.
Then again I’ve been playing with Linux (and using it professionally on the server side) since the 90s, so am not at all representative of most people out there.
Yeah, I have a similar situation with Borderlands 2 not running on my machine with Windows 7 but running just fine in Linux with Proton (which is Steam’s branch of Wine).
It seems to me that Linux with Wine is actually better at backwards compatibility for Windows applications than Windows itself.
PS: Also a handful of old games I have from GoG that wouldn’t run on Windows run just fine with Wine on Linux.