You're completely right, we need to upgrade the Python 2.7 version. The reason we haven't done that so far is that everyone shares the same system image, and so we'd have to upgrade it for everyone -- but unfortunately virtualenvs, when they're created, have symlinks that go to the specific point version of Python. So if we upgraded, we'd break every existing virtualenv on the system, which would be bad...
The fix, of course, is to have different system images for different users (with the option to switch to an upgraded one at a time of the user's choosing) -- and that's the direction we're going in, but it'll take a while.
I've updated the help page, anyway, so hopefully that'll help in the meantime.