> In my opinion, it is a bug in Windows
I don't think calling every complicated API a "bug" is useful. Is the Win32 API exceedingly annoying? I think everybody agrees on that, but imo it's  better to fix this once in python itself and don't force all developers to think about those details.

Fixing this in pathlib is better than not doing anything, although with the large amounts of code out there that use os, it'd be nice if we could fix it at the source (also since I assume pathlib internally is going to call the os module, it's still the same amount of work). 


If I provide unit tests for all the involved file system functions and fix the issues (more work than expected looking at the linked issues, but doesn't seem too hard), would such a patch have chances to be included?