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I've merged the changes from when ensurepip was added to Python 3 into msi.py (and also fixed up the new externals dir location), but I'm no expert on this script, so at least a second set of eyes would be appreciated. It seems to build and work okay.

Issue #22827 was the ensurepip backport.

I don't know anything about msi or this script so I can't offer any help there, but thanks!

This looks to match the relevant pieces of the Python 3 version to me.
However, it occurs to me that Python 2 will still be missing other Windows usability enhancements that make pip easier to use:
- bundling the py launcher
- providing the installer option to enable PATH modifications that add the Scripts directory to the path
I forgot about those when writing PEP 477.

I'm not working on Python 2.7 anymore, so I can't offer help.

After digging a little further, I see Brian backported the PATH modification support from issue #3561 in https://hg.python.org/cpython/rev/a9d34685ec47
This should probably be noted in the What's New document - while it's not technically part of PEP 477, that's still a good home for it in the What's New doc.
The lack of the Python launcher in Python 2 likely isn't a problem - at this point in history, switching between Python 2 and 3 is the most likely scenario, and in that situation, the launcher would have been installed together with the Python 3 installation.

Yes, I'll add Scripts into the PATH when that option is enabled too. I ignored that from the changeset I merged from, forgetting that that's where pip.exe will end up.
I'd rather not bundle the launcher with Python 2 right now (if ever). With the 3.5 installer it's going to be a much smoother ride as far as upgrades go (or having a standalone installer, which is basically what it is), and the more versions that try to fight with that one the harder people will find things.
Hopefully I have time to finish this off tonight, otherwise it may not be done until next week, as I'm very busy the next few days.
(Thanks Brian for the feedback on the review.)

New changeset c248a6bdc1d7 by Steve Dower in branch '2.7':
Issue #22850: Backport ensurepip Windows installer changes to 2.7
https://hg.python.org/cpython/rev/c248a6bdc1d7 

Is this ticket able to be closed now or is there more to do?

It's done.