> I can pull down a 20 year old exe and still run it today on Windows. Try doing the same with a Linux binary that's just a year old. There's no guarantee that it will be able to run based off some update that has happened IMHO, you just compare two different things. Traditional method of installing apps on Windows is packing all dynamic dependencies with it. While on linux dynamic dependencies are shared between app…
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.