Donald Stufft added the comment:

1. This is bound to be an issue that stems from the fact pip is doing the 
install instead of distutils. It probably makes sense to use the group id of 
the parent directory I think?

2. This is a side effect of Wheel being a whole new way to install, previously 
pip just did setup.py install which took care of this bit. It shouldn't be a 
problem to make this happen.

3. Which sdist were you testing? The one from PyPI? We switched the style of 
that in 1.5 in order to better match how Python itself handles it versioned 
commands.

4. You mean when you do --default-install? (Or whatever it's called if Nick 
changed it).

5. I don't think any of us have ever run pip under a debug build of Python so 
that's probably why. It should probably be fixed up.

6. I'm not sure what the right answer is here. We recently switched pip to 
install using the default umask because previously it was using whatever 
permissions where in the archive. If the make file wants to control the 
permissions of the files can't it simply adjust the umask before calling 
ensurepip?

7. See the answer to #2.

8. I'll need to think about this, we don't want to blindly add 
--ignore-installed because we don't want ensurepip to downgrade pip if a newer 
version is installed.

Things that I see as issues so far I've created upstream tickets for, things 
that I still have questions on I didn't.

https://github.com/pypa/pip/issues/1324
https://github.com/pypa/pip/issues/1325
https://github.com/pypa/pip/issues/1326

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