> All of these are at one out of two compromises from being MITM'd during the upgrade.

This is not true; pip supports hash pinning, so an attacker would have to be able to defeat SHA256 as well (or compromise both the official Python discussion forum and PyPI itself, so as to forged the published hash). Other hashes can also be used. Instructions are provided on the Python discussion forum to self-upgrade pip with hash pinning: https://discuss.python.org/t/information-for-python-users-re...