Since you were able to help me scope that this is probably an MacOS specific issue, I was able to find this report:
https://github.com/pytest-dev/pytest-flask/issues/104

Setting `multiprocessing.set_start_method("fork")` _BEFORE_ the code is called resolves this.

I don't understand enough of MP to understand why this is a problem, and why I need to do this, but alas, at least I have a path forward. 


Since this behavior changed, and it _doesn't_ work cleanly anymore with MacOS, I would say this is a bug (from my casual understanding of python), because it's mentioned in the documentation that using "fork" can be problematic and lead to crashes outlined in bpo-33725.
> Changed in version 3.8: On macOS, the spawn start method is now the default.
> The fork start method should be considered unsafe as it can lead to crashes 
> of the subprocess. See bpo-33725.