Helping improve the spec and all is great, but being 100% honest, as a user, I would rather have a type checker I can bend to my needs. As you said, some code patterns in a dynamic language like Python are difficult, or even impossible, to type-check without custom code. Type checkers are becoming more popular than ever, and this implicitly means that these code patterns are are going to be discouraged. On one hand, I believe the dynamism of Python is core to the language. On the other, I would never want to write any collaborative piece of software without a type checker anymore. Therefore, to get the benefits of a type checker, I am occasionally forced to write worse code just to please it.
Considering how fast uv and ruff took off, I am sure you are aware of the impact your project could have. I understand that supporting plugins is hard. However, if you are considering adding support for some popular libraries, IMHO, it would be really beneficial for the community if you could evaluate the feasibility of implementing things in a somewhat generic way, which could be then maybe leveraged by third-party authors.
In any case, thanks for all the amazing work.