Emily Morehouse added the comment:

A quick note on how to include system packages in the "How Do I..?" section 
could be helpful, though does not necessarily solve the current issue. I would 
be hesitant to instruct people to use the system-site-packages flag simply to 
have an updated version of setuptools, even with a strong word of caution. From 
my experience, most people generally don't have a clean pip environment outside 
of a virtual environment for various reasons and this could cause more 
confusion and undesired outcomes by encouraging use use of the 
system-site-packages flag.

As a side note, I do feel that the existing documentation for the 
system-site-packages and without-pip flags is adequate as-is (that was one of 
the first things I tried when debugging this issue).

Nick, could you answer a couple of questions for me? 
1) I've read that (for Python 3.5 or greater) that venv is recommended over 
virtualenv. Why? (Not challenging anything, just trying to understand from the 
perspective of someone who has used virtualenv for years and never looked back).
2) Could there be an additional argument for venv that triggers an upgrade to 
setuptools on virtual environment creation? Alternatively, I've looked into 
extending venv.EnvBuilder. We could add an example of extending this to 
bootstrap environment building to include a setuptools upgrade on creation for 
those who deem this important.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue30628>
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