In pydoc.Helper.__init__ I see this code:
execdir = os.path.dirname(sys.executable)
homedir = os.environ.get('PYTHONHOME')
for dir in [os.environ.get('PYTHONDOCS'),
homedir and os.path.join(homedir, 'doc'),
os.path.join(execdir, 'doc'),
'/usr/doc/python-docs-' + split(sys.version)[0],
'/usr/doc/python-' + split(sys.version)[0],
'/usr/doc/python-docs-' + sys.version[:3],
'/usr/doc/python-' + sys.version[:3],
os.path.join(sys.prefix, 'Resources/English.lproj/Documenta$ if dir and os.path.isdir(os.path.join(dir, 'lib')):
self.docdir = dir
I think the third choice in the list of candidate directories is wrong. execdir is the directory of the Python executable (e.g., it's /usr/local/bin by default). I think it should be set as
execdir = os.path.dirname(os.path.dirname(sys.executable))
You're not going to find a "doc" directory in /usr/local/bin.
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