Since Python 2.7 is only supported until 2020, I decided I should get familiar with Python 3 and set up a Python 3 environment.
That said, there were cases where things like dlib wouldn’t configure properly unless I used Python 2 (although this may also have been my own mistake), so I decided to keep both around and build virtual environments for each.
Environment
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$ sw_vers
ProductName: Mac OS X ProductVersion: 10.11.5 BuildVersion: 15F34