I'm on the other end of the spectrum — I only write Python occasionally for smallish utility tools, just a step above shell scripts — so I'll give my input as someone relatively new to typed Python. I recently industrialized (to use the terminology from other comments here) a couple things that I'd originally done in quick-and-dirty Python 2 over a decade ago. My experience was that mypy had a handful of false positives, and pyright had none. Pyright also found one comparatively subtle mismatch that mypy didn't, although its error message in that case was incomprehensible to me.
(I also used pylint and pytest+coverage.py; interested whether there are better choices for next time.)
(I also used pylint and pytest+coverage.py; interested whether there are better choices for next time.)