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- For me, running a virtual copy of an ancient system let me avoid
  buying a new license when the old machine wasn't worth running any
  longer.

- NixOS would seem to address this.  Is that its justification?

What do real businesses do?  What should they do?
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There is an important subset of computing out there that does something rather interesting with this.

Machine tools run old versions of Windows. I'm not in the field at present but I know that not too many years ago it was like DOS was still alive and a small subset of the available control software ran on a Windows system. Likely things have moved forward somewhat but when I was working on things the software was at least 15 if not 20 years behind.

Many large businesses are still running on NT 3.51 (IIRC  (the version numbers)).
When you are at your bank look at the screen - - - its Win XP.

If the software does what you want it to do why change for the newer - - - big business has always done that.

I'm very much of the opinion what change for changes sake is a waste of effort.

Dee