> What's the best way to keep all these python pieces up to date?

There is yolk (available on pypi.python.org) to check for updates.

As to updating all that need updating, there are some suggestions along
the lines of:
pip freeze --local | cut -d = -f 1  | xargs pip install -U

But you might experience some rough edges around that solution. A request
to add the functionality to pip seems to be stuck in the pull request
queue:
https://github.com/pypa/pip/pull/313