pip is easily the worst thing about Python. But now that we have uv I would say the worst thing is the package/import system. I'm pretty sure only 1% of developers understand it, and it only really works properly if your Python code is a Python package.
If you treat Python as a scripting language and just scatter loose files around your project and run them directly, it doesn't work at all. Pain everywhere. Which is dumb as fuck because that's like 80% of how people use Python.