

Some win95 / win98 software doesn’t work all that well on Windows 10/11. It’s mostly stuff that was targeted for the early releases of Windows and cannot be run in DOS (or the DOS version is more primitive than the Window aversion).
One example:
https://archive.org/details/biestystowaway
It’s mostly games and random educational releases like the one above.
I am not that well acquainted with WINE, but I do know there are examples where WINE does not work well.