Doesn't windows have a standard windows installer for python? Why are we still teaching beginners Python 2.7? What is wrong with python 3?
For example, PIL doesn't support Python 3, but there's a GraphicsMagick wrapper [1] which does. Graphics Magick is more functional anyway.
You may have time invested in PIL and other Python 2 libraries, but newbies don't, and there's no reason to start them off on a dying version of the language. It's contributing to the chicken and egg problem that's holding Python back.
Someone who only knows Python 3 would have a hard time hacking on the source code of most libraries.