Might be some things to learn from paulross/typin

Here is a similar project with some of the same goals as pyannotate: https://github.com/paulross/typin

There might be something useful in there for you. Injecting type aware documentation strings for example: https://github.com/paulross/typin/blob/master/src/typin/types.py#L537

Now that I have discovered `pyannotate` I doubt I will progress `typin` as it was just a side project!