> `os.path.expanduser` in `ntpath` uses `HOME` in preference to 
> `USERPROFILE` / `HOMEDRIVE\\HOMEPATH`

Guido intentionally added support for HOME in ntpath.expanduser way back in Python 1.5 (circa 1997), and now we're removing it over 20 years later. I expect this to break some deployments, but it's not a serious problem. 

My feeling here is "meh". Practically all use of expanduser() is dubious in Windows, varying from going against convention to being completely wrong. We're long due for a module in the standard library that abstracts access to platform-specific configuration and special directories, but attempts to adopt one keep losing momentum. I guess it's too prone to bike shedding and arguments.