Sunday morning I posted "Adding a Pip GUI to IDLE and idlelib (GSOC project)" to the pydev list requesting that any objections to the current plan be raised and resolved soon, before final acceptance of a  student proposal and official initiation of work on it.

About ensurepip (point 1a on Raymond's list): ensurepip is a package in the stdlib.  Regardless of how we later run pip, its presence can be tested on startup by trying to import it. If not present, we should ask whether to install it or nor.  It can be installed either by running 'python -m ensurepip' in a subprocess or by doing what ensurepip.__main__ does:
  import ensurepip; ensurepip._main