I think some of the problems were self-inflicted by trying to use Python on a Mac with no package manager, and on Windows. Things will get easier on the Linux side with Python 3 in repositories now. But it really seems like a fairly common pattern for languages / programming environments is to install the languages package manager and upgrade packages separately from the OS package manager. For whatever reason this seems like a bigger headache with Python than others.
But seriously, mirror your production environment for local development and testing. This is all comically easy with VMs, you just need to alter your workflow.
If pip doesn't work on Windows then it shouldn't ship on Windows. This isn't Windows' fault.
Granted this was recently, under windows 8.1 (tried it mostly for fun, and so that I have a decent calculator (ipython) on hand when I boot up in windows).
import pip
pip.main("install ipython".split())
of course, python for windows drops pip in the scrips-folder -- but doing everything from inside python is magically cross-platform :)Pip will drop ipython in the scripts-folder too -- so that where one can grab a shortcut. Or just (after restarting python):
import IPython
IPython.start_ipython() # Ed: not .start()
[1] http://tutorial.djangogirls.org/I was also pleasantly surprised, building python C extensions under Windows is easy. Building some of the C or Fortran dependencies, on the other hand, might be not.