@Brett: Honestly.... I don't think it is the best way. But fact is:

nono@ACER ~ % cd /

nono@ACER / % python
Python 3.7.3 (default, Mar 26 2019, 21:43:19) 
[GCC 8.2.1 20181127] on linux
Type "help", "copyright", "credits" or "license" for more information.

>>> from pathlib import Path
>>> Path('.') == Path('/')
False

In my humble and *very personal* opinion, this result could be understood in the case of
a PurePath (or some kind of system call free) object. But that is not what people expect
in the case of a 'normal' path...

I also think that one day we may see the rise of a new Os that wouldn't use . and  ..
The first Unix used 'd' for directory and 'dd' for directory's directory !
Those were hand-made links in a file system that otherwise had no concept of hierarchy...

I think each flavour should have a special_dirs variable (fact that linux and MsWin share
the same being an accident). And that the concept of a system-call free path implementation,
is fragile.