My experience has been different: last year I started writing Python again after a long break, and I am yet to regret using types pervasively. If some library has no type definitions, I prefer to have my typed code interact with its untyped code. It is still better than having no types at all. You can sometimes get some useful type safety by annotating your functions with the untyped library's classes.
Since then, I have used established libraries like Beautiful Soup, Jinja, Pillow, platformdirs, psutil, python-dateutil, redis-py, and xmltodict with either official or third-party types. I remember their types being useful to varying degrees and not a problem. I have replaced Requests with the very similar but typed and optionally async HTTPX. My most objectionable experience with types in Python so far has been having to write
root = cast(
lxml.etree._Element, # noqa: SLF001
html5.parse(html, return_root=True),
)
Admittedly, I don't use Django. Maybe I won't like typed Django if I do. My choice of type checker is Pyright in non-strict mode. It seems to usually, though not always, catch more and more subtle type errors than mypy. I understand that for Django, mypy with a Django plugin is preferred.