And don't get me started on eggs. I guess the nice thing about Python is that the packaging genuinely seems to be improving year-to-year, although still limited by design decisions and backwards compatibility.
Anyway, thanks for this; I've had a pretty informative morning searching for "npm vs pip". I'm not a Javascript dev, and when I've tried to use it I've struggled with the sheer bloat, even e.g. npm vs bower. Even though I'm a bit jealous of npm now, I'll take pip over package management in the usual enterprise juggernauts (C, C#, Perl or Java) any day!
That's actually not what I'm talking about, though, since ultimately those are just DX conveniences. The big difference is that, by default, npm installs dependencies in a nested rather than a flat manner. This means that you can install "library A" and "library B", which both depend on "library C", without worrying about potential incompatibilities between the required versions of "library C". This isn't possible in Python; one consequence is that you see a bunch of libraries that vendor their own small subsets of six to avoid having potential dependency issues – you don't get this in the Node ecosystem, because you can just pull in that dependency and not worry about potential version conflicts.
All of this adds up to a much nicer experience when developing libraries.
For example, Python's lack of support for nested dependencies means that it can be extremely difficult to use small "utility" libraries like six as subdependencies without running into potential problems from conflicting version requirements from other dependencies.
Additionally, Python's management of different types of dependencies is very weak, specifically with regard to setup.py and requirements.txt. npm has (among other things) very nice explicit concepts of development dependencies and regular dependencies, in addition to application shrink-wraps, which gives library maintainers very easy ways to split out different kinds of dependencies, or lock down all dependencies and subdependencies, using the same set of tools.
While I can say that the current version of pip, especially in conjunction with pip-tools, is significantly better than earlier iterations of Python packaging, I strongly hold that Python packaging is substantially worse than at least one other prominent example.