As a static typing advocate I do find it funny how all the popular dynamic languages have slowly become statically typed. After decades of people saying it's not at all necessary and being so critical of statically typed languages. When I was working on a fairly large TypeScript project it became the norm for dependencies to have type definitions in a relatively short space of time.
JSON's interaction with types is still annoying. A deserialized JSON could be any type. I wish there was a standard python library that deserialized all JSON into dicts, with opinionated coercing of the other types. Yes, a custom normalizer is 10 lines of code. But, custom implementations run into the '15 competing standards' problem.
Actually, there should be a popular type-coercion library that deals with a bunch of these annoying scenarios. I'd evangelize it.