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I agree that a proper solution might include full symlink support.
However, symlink support for windows (issue1578269) is taking some time
to develop and will likely never be available for Python 2.
My feeling is that a symlink naive implementation (such as Python is
now), should treat symlinks in a naive manner -- that is, treat them as
regular files and directories and let the OS perform the abstraction.
I hope to begin investigating this after I've closed out issue1578269,
although I'd be happy if someone else wanted to address this issue
beforehand.
If it's possible to address this in a straightforward way independent of
a symlink-aware Python interpreter, that would be desirable.