Nick Coghlan added the comment:

Right, I think we need to separate two questions here:

1. Making a GUI for pip available *at all*. At the moment, there isn't really 
one, so even if instructors want to offer one, they can't without writing it 
first. That's a reported PyPA issue here: 
https://github.com/pypa/packaging-problems/issues/57

2. Whether to endorse and bundle such a GUI with CPython, and integrate it with 
IDLE.

I think the first aspect is an unequivocally good idea, and I'd encourage 
Upendra to head down that path to make it available to folks that are 
interested in having a cross-platform GUI for working with pip packages, 
regardless of what happens on the CPython integration front.

For the second point, I'll note that Donald was a trusted *PyPA* developer 
prior to our collaboration on PEP 453 - he became a CPython core developer 
specifically to maintain ensurepip.

I believe that "cross-community collaboration" model would also be a good fit 
for integration of a pip GUI distributed that was otherwise distributed via 
PyPI - we'd want core developers, or folks trusted by core developers, 
reviewing and maintaining the PyPI package, without necessarily pulling it 
directly into the CPython maintenance workflows.

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