Yup, python's packaging is even awful for the users. Half of the time pip cannot determine what version of a package to install for a given version of python on its own. "pip install --upgrade"? Gross.

However, you know what else needs improvement? PyPi. PyPi is downright embarrassing compared to rubygems, npm, etc... and not only needs a facelift but a whole redesign. This is the reason that I absolutely love to use python but dread using a python library that I haven't heard of 1st hand. Treading outside the standard library is an exercise in sifting through garbage.

Want to see which package for a "x" is most popular? No problem for any dynamic language besides python. However, search for "http" on pypi and you'll get a list of packages by weight which does not take into account popularity or download count or views, just the score of a textual match.

Why is that important? Well when you search for "http" you get these as pypi's top choices (no help at all):

    http               0.02
    CydraGitHTTP       0.1
    django-http-status 0.2

So what do we have here? A beta library (version 0.02) called "http" ranks 11 (off the charts) while kenneth reitz's insanely popular "requests", which should be mandatory as an http client library, is nowhere to be found.

Pypi isn't even serving up the latest version of the python packages it has some of the time (see: SCons).

All of this leads me to think the Pythonistas have given up on PyPi which does more to hurt the community than you can imagine: It leaves a bad taste in the mouths of those looking for quality libraries and software when they reach for Python as their tool of choice.