Serhiy Storchaka <storchaka+cpyt...@gmail.com> added the comment:

I think you are trying to solve a wrong problem.

> This wasn't obvious because Path objects appear as strings in normal debug 
> output, etc.

How is it?

>>> pathlib.Path('/usr/lib')
PosixPath('/usr/lib')
>>> [pathlib.Path('/usr/lib')]
[PosixPath('/usr/lib')]

I think the problem is with the debug output. Always use repr() for it, 
otherwise you will trick yourself.

> but the corresponding imports weren't working as they should

It would be easier to catch if it was never working with non-string. I think we 
should deprecate any non-string elements in sys.path.

As I shown above some code only works correctly with strings anyway.

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<https://bugs.python.org/issue32642>
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