Hypothesis can report statistics on user-defined events, as well as the usual timing stuff: https://hypothesis.readthedocs.io/en/latest/details.html#tes...

I'd just check that when you're writing or changing the tests though; for nontrivial conditions it can take a very long time to get neglibible probability of any metatest failing in a given run, and flaky metatests are just as bad as the usual kind.

If this split is particularly important, we'd usually recommend just writing separate tests for data that satisfy A or B; you can even supply the generators with pytest.mark.parametrize if copy-pasting the test body offends.