I’m sure the PyPA has done of ton of nice and useful things, but “some kind of cohesive vision to rally around a central, official, out-of-the-box workflow” doesn’t sound like it. On the contrary, the PyPA seems to openly go for an ecosystem of scattered utilites with partially overlapping goals (not to mention the diversity of configuration schemes that goes with it).
Bootstrapping a Python project always leads to looking around the Internet for clues as to “the idiomatic way”, only to find out that there is none and that you have to make a half-informed choice between multiple possibilities (not to mention multiple documentation sources emphasizing different practices).
And I say that as a Python core developer. I have no idea how frustrating it might be for the occasional Python developer who was hoping to do the Right Thing without hassles.