I was involved in replacing Windows systems with Linux + Wine, because (mission-critical industrial) legacy software stopped working. No amount of tweaking could get it to work on modern Windows system. With Wine without a hitch, once all the required DLL files were tracked down.
While Wine may indeed be quite stable and a good solution for running legacy Windows software. I think that any dynamically linked legacy software can cause issues, both on Windows and Linux. Kernel changes may be a problem too. While Windows is often claimed to be backwards compatible, in practice your mileage may vary. Apparently, as my client found out the hard/expensive way.