I just had a nice conversation on #pypa-dev re ensurepip, which is part of Python 3.4 and will also be bundled in PyPy 2.3, which supports both 2.7 and 3.4 versions of Python. I recommend that Jython 2.7 do the same, given that like PyPy we are under active development, unlike CPython 2.7.
We should be able to do this in time for beta 4.
ensurepip (https://docs.python.org/3/library/ensurepip.html) provides support for having a bundled version of pip, which is then used to install the current version of pip in a matter that's transparent to the user. Jython simply needs to bundle the required pip and setuptools wheels and the ensurepip package in stdlib.
This will mean that our users will have pip immediately available to them upon installing Jython, with no extra steps required. PyPy has done the hard work to provide a 2.7-compatible version. More rationale here: http://legacy.python.org/dev/peps/pep-0453/
This timeline depends on a pull request I made against pip's vendor lib dependency html5lib-python getting made, but I don't expect us to see any blockers there.