I find that unless that software needs access to hardware, or is very performance sensitive or uses some newer Windows APIs, most of the time Wine can run it. I still have Windows installed for those few things that require it. But over time that has become less and less.

I even had to grab the TP-Link easysmart configuration utility yesterday to configure an old managed switch and the exe ran perfect on Wine. I was honestly quite surprised. In fact I first started it up and it didn’t detect anything and I was afraid it was incompatible, but turned out the second NIC in my PC was just set up on the same config in network manager because I had been playing around with some stuff. It also runs the old Windows Epson Scanner software and drivers that my old scanner requires that no longer work in Windows 11.

Anyway, for old proprietary stuff I find that Wine emulates older Windows and DOS better than Windows 10 or 11.