Let me start by saying: I love python, and I love developing in it. It's the "a pleasure to have in class" of languages: phenomenal library support, not too painful to develop in, nice and lightweight so it's easy to throw together test scripts in the shell (contrast that with Java!), easy to specify simple dependencies + install them. (contrast that with C!).

That said... if you work on software that is distributed to less-technical users and have any number of dependencies, python package management is a nightmare. Specifying dependencies is just a minefield of bad results.

- If you specify a version that's too unbounded, users will often find themselves unable to install previous versions of your software with a simple `pip install foo==version`, because some dependency has revved in some incompatible way, or even worse specified a different dependency version that conflicts with another dependency. pip does a breadth-first search on dependencies and will happily resolve totally incompatible dependencies when a valid satisfying dependency exists.[1]

- If you specify a version with strict version bounds to avoid that problem, users will whine about not getting the newest version/conflicting packages that they also want to install. Obviously you just ignore them or explain it, but it's much more of a time sink than anyone wants.

- In theory you can use virtualenvs to solve that problem, but explaining how those work to a frustrated Windows user who just spent hours struggling to get Python installed and into their `PATH` is no fun for anyone. Python's made great strides here with their Windows installers, but it's frankly still amateur hour over there.

- Binary packages are hell. Wheels were supposed to make Conda obsolete but as a packager, it's no fun at all to have to build binary wheels for every Python version/OS/bitness combination. `manylinux` and the decline of 32-bit OSes has helped here, but it's still super painful. Having a hard time tracking down a Windows machine in your CI env that supports Python 3.9? Too bad, no wheels for them. When a user installs with the wrong version, Python spits out a big ugly error message about compilers because it found the sdist instead of a wheel. It's super easy as a maintainer to just make a mistake and not get a wheel uploaded and cut out some part of your user base from getting a valid update, and screw over everyone downstream.

- Heaven help you if you have to link with any C libraries you don't have control over and have shitty stability policies (looking at you, OpenSSL[2]). Users will experience your package breaking because of simple OS updates. Catalina made this about a million times worse on macos.

- Python has two setup libraries (`distutils` and `setuptools`) and on a project of any real complexity you'll find yourself importing both of them in your setup.py file. I guess I should be grateful it's just the two of them.

- Optional dependencies are very poorly implemented. It still isn't possible to say "users can opt-in to just a specific dependency, but by default get all options". This is such an obvious feature, instead you're supposed to write a post-install hook or something into distutils.

- Sometimes it feels like nobody in the python packaging ecosystem has ever written a project using PEP420 namespaces. It's been, what, 8 years now? and we're just starting to get real support. Ridiculous.

I could go on about this for days. Nothing makes me feel more like finding a new job in a language with a functioning dependency manager than finding out that someone updated a dependency's dependency's dependency and therefore I have to spend half my day tracking down obscure OS-specific build issues to add version bounds instead of adding actual features or fixing real bugs. I have to put tons of dependencies' dependencies into my package's setup.py, not because I care about the version, but because otherwise pip will just fuck it up every time for some percentage of my users.

[1] I am told that this is "in progress", and if you look at pip's codebase the current code is indeed in a folder marked "legacy".

[2] I 100% understand the OpenSSL team's opinion on this and as an open source maintainer I even support it to some degree, but man oh man is it a frustrating situation to be in from a user perspective. Similarly, as someone who cares about security, I understand Apple's perspective on the versioned dylib matter, but that doesn't make it suck any less to develop against.