On that note, the PUG index currently feels a little overwhelming

The main index is 2 levels deep currently. Let me drop it to one level and see how that looks.

I personally like a deep index as my main entry point to docs, but I can see it being a bit much.

the point of view of someone who just wants to get a job done. it's
got a lot of "Getting started with X" and "What is" sections, but
nothing like "Installing a package from PyPI" or "Starting a new
project". Maybe the index should be reorganised to be more
task-oriented, and less concerned with providing history and
background to the confusion that led us to where we are now?

2 things:

1) In my opinion, a big part of the PUG is about "deconfusing" people, and giving confidence that there's consensus on what to do now (with a justification), and there's plans to move forward. That's what many people need and will come to the PUG for. They already know the basics of pip and setuptools.

2) As for providing basic pip/setuptools tutorials, I've taken the position that the PUG shouldn't do it, but instead defer with links. The project docs themselves should have tutorials, so let's just do it once, and right, and link to it. Supposing you still thought it was a good idea for both to maintain tutorials, practically speaking, I think it will fail. One, or both will end up being not maintained or inconsistent with each other in the long run. I want to construct something that has a good chance of persisting and staying up to date. We have access to the 4 main projects, and can get PRs through. There seems to be an unspoken idea that we can't update the setuptools docs. We rely on setuptools heavily, and it has years of life left in it. The docs can be first rate, and consistent with what's currently going on.

But in saying that, I'm still open to other TOC ideas. It is an open project. But with any idea, I'd like to see a full breakdown of the alternative TOC and how it covers everything we have now.