The biggest problem in Python dep management is Pip. When upgrading pip breaks tools wrapping/integrating with it, it's a bad time. I've had to pin pip itself

The biggest problem in Python dep management is Pip. When upgrading pip breaks tools wrapping/integrating with it, it's a bad time. I've had to pin pip itself a few times due to resolution that used to work failing, and sometimes there's breaking API changes at the module level. Oh and also because setup.pys in packages are somehow tied to pip apis. It's a weak foundation to build from.