a reasonable percentage of the time it doesn't work correctly.

The pypi web interface is very poor.

There is lots of scope for improvement in locating and installing packages.

(though I agree it is as intuitive, at it's most basic, as ruby gems)

And that's about all it does. You have to update packages manually and you can't remove them at all with easy_install. What's so beautiful about gem to me as a Python dev is this:

$ gem update && gem cleanup

A lot of headache I don't have to deal with at all. I really wish Python would grow an equivalent tool.

The most unintuitive thing is that there's no easy_uninstall.

That's it's completely python specific. All Java and perl modules are typically installed via JPackage and cpan2rpm, there's no justification for Python to need its own unique non-native package management method.