One thing that make Windows paths wired is that Windows API, NTFS and most Windows tools have different restrictions on file paths.

NTFS would accept almost anything. The Windows API (I think of the old Win32 one) would apply most restrictions the article mentions.

But for example not the normalization part. A filename can end with a space, no problem. That lead me once to a minor bug in .NET Framework. One of the path related functions (I think it was Directory.move) did not correctly apply this normalization and could produce directories with trailing whitespace. Good luck removing/fixing those in Windows Explorer.