For 8 in particular, I'm inclined to push that over to the pip side of the fence (as with the first 7 points). pip knows that ensurepip is involved (due to ENSUREPIP_OPTIONS being set in the environment), so it may be able to check if the unversioned scripts are missing and generate them appropriately in that case.

How do we want to proceed for the first beta? Given the integration timeline in the PEP (which doesn't require the shipped version of pip to be locked until just before beta 2), I'm inclined not to consider the additional quirks Ned found as blockers for beta 1, but we do need to get them fixed for beta 2.