In principle yes it’s worth it even for more complex data. In practice, hypothesis is not good at this (I would argue it is broken currently, as specifications

In principle yes it’s worth it even for more complex data. In practice, hypothesis is not good at this (I would argue it is broken currently, as specifications that are valid can fail for… reasons of implementation details) and the maintainers don’t think there’s any problem with this limitation. I’ve had much better luck with generative testing in clojure and haskell.