So I tried making pathlib.PurePath handle "." more like ".." and tests started failing all over the place in test_pathlib, which means it would be a change in semantics and could start silently breaking people as most of the checks are for specific exceptions.

So the next question is where is '..' being mishandled? It might be possible and better to tighten up how '..' is treated than try to make '.' suddenly be treated in a weaker way.