A lower barrier way of trying this out could be to run MonkeyType in combination with OP's hypothesis-auto (which uses type annotations to generate the tests).
[1] https://github.com/google/pytype
[2] https://github.com/dropbox/pyannotate
[3] https://github.com/Instagram/MonkeyType
[4] https://news.ycombinator.com/item?id=19454411
A lower barrier way of trying this out could be to run MonkeyType in combination with OP's hypothesis-auto (which uses type annotations to generate the tests).