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During our development we have experience the following:
If you have a user in your Windows machine with a name hat uses Japanese characters like "雄鳥お人好し" you will have the following in your system:
* The Windows Shell will show the path correctly, that is: "C:\Users\雄鳥お人好し"
* cmd.exe will show: "C:\Users\??????"
* All the env variables will be wrong, which means they will be similar to the info shown in cmd.exe
The above is a problem because the implementation of expanduser in ntpath.py uses the env variables to get expand the path which means that in this case the returned path will be wrong. 
I have attached a small example of how to get the user profile path (~) on Windows using SHGetFolderPathW or SHGetKnownFolderPathW to fix the issue. 
PS: I don't know if this issue also occurs on python 3.

On POSIX, Python 3 works correctly if my home dir is /tmp/éric, and Python 2.7 returns a UTF-8-encoded (not locale-encoded!) bytes string.
For Windows, a patch would probably need to add a private function to the _nt module (in C): ctypes is too dangerous to be used in the standard library.

Unicode environment vars work properly in Python 3.x on Windows, too, because the convertenviron() function in posixmodule.c uses extern _wenviron PyUnicode_FromWideChar() in Python 3.x. In Python 2.7, convertenviron() uses extern environ and PyString_FromString*().

Python 2 uses byte strings. If characters are not encodable to the ANSI code page, Windows replaces them by question marks. See the issue #13247 for another example (in Python 3 when using explicitly the bytes API). To be able to support characters not encodable to the ANSI code page, you have to use Unicode *everywhere*.
Because Python 2 doesn't have access to the Unicode environment and uses bytes in most cases, I don't think that we can fix this issue in Python 2.
I close this issue because it would require too much work to fix this issue in Python 2, whereas it already works in Python 3. Move to Python 3 is the best solution of this issue.

At least Python 2.7 should return in locale.getpreferredencoding() encoding