Software doesn't degrade over time (other than, you know things like cosmic ray bit flips, but in most realistic situations that should be fully mitigatable.)
The needs of the software user (including hardware and software they want the piece of software to interact with) may evolve, but that's different than software degrading over time.
> I had a stack that worked just fine for my own needs, but it ran on shudder Python 2.7 -- everyone knows how that worked out
While there's no further first party support for that version of Python, if it worked properly before, Python 2.7 and the software running on it probably still works properly now.