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I take it you're doing a lot of greenfield projects with the latest versions of Python then. I've encountered issues with Setuptools as recently as ~3 months ago:

https://github.com/pypa/setuptools/issues/2352

I've also had to play the pip version pinning game a few times in the past.

Here is one from September:

https://news.ycombinator.com/item?id=24336058

That one looks like an issue with the debian package trying to alter paths and blowing things up.

There's definitely recurring issues with distributions trying to handle python dependencies, which doesn't match how python handles dependencies.

Same here.