Unless it's (maybe) mainfraame software, your software is going to break with an OS update. O you can maybe keep it working for a while in a VM, but the idea that you'll keep a software binary working forever is, for practical purposes, mostly silly.
Windows backward compatibility counter example: Paint Shop Pro 7.04 still works great here after almost a quarter century.
Somewhere buried on the Microsoft site there is a page that says they are committed to getting any 32bit windows software or above working and they have a separate support team for. I assume they are the Compatibility team.