Thanks for the report. Point 2 is definitely a bug (and an overlook by me), I will fix it.

I think, the url[:2] == '//' check was present for ftp case which supported file:// protocol. I can't see a clear requirement to change here.

The scenarios you encounter when giving a two different paths are interesting because, in one the path stat('/invalid/path') and in the other it is the path '/' that is stat and only late is the hostname verified if it coming from localhost (http://hg.python.org/cpython/file/ddfcaeb1c56b/Lib/urllib/request.py#l1353). 
Since both presence of file locally and then ensuring the host is localhost needs to be done, the current order gives faster failures for most common use-cases.