Every time I'm doing anything with Python I ask myself if Java's tooling is this complicated or I'm just used to it by now. I think a big part of the weirdness is that a lot of Python tooling is tied to the Python installation whereas in Java things like Maven and Gradle are separate. In addition, I think dependencies you install get tied to that Python installation, while in Java they just are in a cache for Maven/Gradle. And in the horrible scenario where you need to use different versions of Maven/Gradle (one place I was at specifically needed Maven 3.0.3 for one project and a different for a different, don't ask, it's dumb and their own fault for setting it up that way) at least they still have one common cache for everything.

I guess it also helps that with Java you (often) don't need platform specific jar files. But Python is often used as an easy and dynamic scripting interface over more performant, native code. So you don't really run into things like "this artifact doesn't have a 64 bit arm version for python 2" often with Java. But that's not a fault of Python's tooling, it's just the reality of how it's used.