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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.