Re:Pip has dropped support for Python 2
by Blikkentrekker on Sunday January 24, 2021 @10:51AM
(#25892966)
I do believe that such a trivial change would indeed be fine. If one can go to the effort of installing the new version, one can add one line in a configuration file to depend upon old behavior.
You're still breaking code by default this way, but no one would have trouble updating.
My concern is that, if you don't make the preferred behavior clear, a lot of people would simply never adopt it. I don't think that Python's userbase in particular is going to spend time reading documentation on best practices.