— Consider using Pydantic (either its drop-in dataclasses replacement, or its models). It has issues and documentation is lacking in places, but in many use cases it’s a boon when it comes to being confident about data you read and/or pass around.
— Don’t use TypedDict if you foresee needing anything like optional keys, especially with defaults. I went with TypedDict and it came back to bite me later (though was relatively easy to refactor).
— Keep an eye on https://pypi.org/project/typing-extensions/, it has some useful utility types. I wish I knew about this package a couple of months back.
— If you use VS Code (which I started after switching to TS), there’re some shenanigans to be aware of. Unlike TypeScript’s elegant approach where you’re in control of installing typing versions, VS Code’s official Python extension will force-install unvetted third-party typings, not caring if they don’t match library versions in your use and not allowing to opt out. In later versions you can unset mypy in Python extension settings, and use a separate Mypy extension that doesn’t do this behind your back and doesn’t send you deep into some rando’s typings when you hit F12 to jump to definition.
— That aside, VS Code can provide development experience is not that far from TypeScript. You can keep a virtualenv nearby and select its Python bin as interpreter in your workspace, giving Mypy access to dependencies (and if VS Code’s interpreter selection GUI resolves symlinks, you can enter interpreter path by hand so that it doesn‘t).
— Sphinx documentation is good at picking up typing hints and works reasonably well with Pydantic’s models, too.
The only one which stands out to me as non-trivial in TypeScript is thrown exceptions… and even then only because you can only type them in a catch clause, and only with unknown, and they’re invisible to callers. But then this is why people who would care for checked exceptions quite reasonably just use something like a Result type.
But I agree with your conclusion completely, and it’s basically the same one I came to reading the post.
I was curious about how the current state of things compares to TS, as I may soon have a foray back into Python soon, and would be delighted to bring some static types into the mix. Pretty much as I expected, it’ll probably be more effort/less valuable than TS, but more valuable to me than to the author.