I agree that we need a better pprint. I think it would be easier to create something new rather than try and morph the existing pprint, but maybe I lack enough imagination. I'd prefer to use functools.singledispatch instead of a __pprint__ method, but it doesn't really make a lot of difference. PEP 443 (singledispatch) does use pprint as a motivating example.

I tend to agree with Raymond that we don't want to guess what a dataclass class intends as its usage. After all, we deliberately made it easy to add a custom __repr__ (one not generated by dataclasses.dataclass).