Having migrated my application's Python and JS codebases to their typed siblings respectively last year, my 2c is that Python typing feels good and worthwhile when you're in the standard lib, but _awful_ (and net-negative) once you leave "normal Python" for the shores of third-party packages, particularly ones that lean heavily on duck typing (Django and BeautifulSoup both come to mind.)
This is where some of the stuff in the TypeScript ecosystem really shines, IMHO — being able to have a completely typesafe ORM such as Drizzle (https://orm.drizzle.team/) feels like a Rubicon moment, and touching anything else feels like a significant step backwards.
This is where some of the stuff in the TypeScript ecosystem really shines, IMHO — being able to have a completely typesafe ORM such as Drizzle (https://orm.drizzle.team/) feels like a Rubicon moment, and touching anything else feels like a significant step backwards.