I had to come back to Python after working with TypeScript for a while. After going from Python 2.x to TypeScript and being very impressed with static typing, I didn’t want to go back to untyped so I had to get up to speed with the ecosystem. My findings:

— 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.