Some tests hang on Windows
Currently, several tests hang on Windows if the max path limit of 260 characters is not disabled. This happens due to the changes introduced by #2223 that cause an infinite loop in `WindowsFileLock` described in #2220.  This can be very tricky to debug, so I think now is a good time to address these issues/PRs. IMO throwing an error is too harsh, but maybe we can emit a warning in the top-level `__init__.py ` on startup if long paths are not enabled.
