One thing that’s unclear to me in this discussion is, what exactly do we want this hypothetical new system to do? I really liked @johnthagen’s example in another thread laying out some concrete examples of things that people might do, but it seems this thread has moved in a more abstract direction.
I think it is not so important to users whether the hypothetical unification is technically “one tool” or several, as long as they are designed coherently as an integrated set. As far as messaging, personally I think one thing that would go a long way toward making users feel like their concerns have been heard and that pip (or whatever set of tools) is responsive to them is a definitive section within the python.org docs that clearly lays out how to accomplish concrete tasks, clearly states that the way it lays out is the official way, and backs that up by clearly demonstrating how to accomplish all the tasks that people want to accomplish but that currently require navigating a labyrinth of conflicting toolsets. (In effect this would be a flowchart that includes choices like “does your project include code written in a language other than Python? if so, then do blah blah”, although it wouldn’t have to be structured like a graphical flowchart.)