pip is unfortunately a a bit hit and miss on Windows. The (IMO) 'correct' way to install package on windows is to first install Anaconda Python (https://www.continuum.io/downloads) and then:

0) Check if the package came preinstalled with Anaconda

1) if not try to use conda to install packages,

2) if conda doesn't have the package, see if it's been uploaded here: http://www.lfd.uci.edu/~gohlke/pythonlibs/

3) try pip.

It definitely doesn't. People writing Python packages make reasonable assumptions like that you've got a POSIX command line, a UTF-8-compatible terminal, and a C compiler that's compatible with the Python development headers. On Windows, you probably don't.

It'd be nice if Windows made an effort to provide a sane environment for Python, because the Python devs certainly aren't doing anything to make things sane on Windows.

Don't you want to try Cygwin? You'll get as close to Unix on Windows as possible. pip will definitely work.

Ubuntu server VM in vbox with shared folders works better than anything I've tried to get things working well I native Windows. Sure it's not impossible, but the tax isn't worth it IMO.

Many things are still broken in cygwin still. Examples: uwsgi, gevent

You need to manually add the directory containing pip and other tools to the path.

If it is not, you can often do python -mpip install xxxxx

And you're right there are some gotchas - for instance pip install -U pip won't work to update pip itself as on Windows a program can't seem to overwrite it's own executable.

AFAIK (and I have dozens of virtualenvs running on a Windows box) you can upgrade pip, it's just one of a handful of packages that throws an error at the end because it was unable to delete the folder it created during the install process. The upgrade works, it just looks like it doesn't. But maybe that's only true inside a virtualenv.

I'm under the (quite possibly mistaken memory) impression that the Enthought guys (ScipPy and NumPy) hid installation stuff behind a GUI for Windows people.

I could be wrong as it's been a long time since I helped anybody with that on Windows.

It is up to whoever creates the package. You can create windows installers with setuptools, see: https://docs.python.org/2/distutils/builtdist.html