Comment by fer

This is my decision flow and I rarely have an issue:

    Are you the end user of the Python code?
        Yes -> Is available in your distro?
            Yes->Use package manager
            No->Use pip install in user mode
        No -> Create virtualenv with the Python version you want (including pypy!) and do your pip thing there

Some extreme use cases may benefit from anaconda, but personally I've never needed to use it. My only pain point is dealing with legacy code that relies on PYTHONPATH. Nothing good ever starts setting PYTHONPATH.