Earlier quoted context omitted.
It's an unfair fear since architecturally Wine sits at the same position as the Win32 API on Windows, which also in the end merely uses the underlying native system calls. The only difference is that Linux aims to keep its system call interface stable.
You're saying that Windows' system interfaces aren't stable? In comparison to Linux?
If a program didn't work on a newer version of Windows, there's a good chance it was doing something unsupported.