The reason for the conditional approach was to attempt to account for the "negative consequences" of adding enabling this by default. i.e. if you are already a Python developer and install a new version, it will be status quo, but if you are a new Python developer then you will be able to run instructions for packages that work perfectly fine on Windows but are maintained and documented by POSIX users and don't understand that the steps to make things work on Windows are different.

I don't care one way or the other about the compromise position but I strongly believe that if someone is installing Python on Windows for the first time they should get a good experience without having to know of the existence of docs like: http://docs.python-guide.org/en/latest/starting/install/win/

This tweet https://twitter.com/#!/zedshaw/status/194853198006198272 is characteristic of the sentiment that non-Windows users have about training Windows users to develop with Python. At the PyCon web summit several people who have been doing training lately have said that their solution is to get windows users to run a Linux Virtual Machine because the Windows Python experience is so bad for new Windows developers. This is one relatively easy place where we can make that experience better.