In my experience it's more annoying than you think, especially if you want to prevent small sneaking regressions.

Python not being statically typed also means all of the breaking type changes they made with string now being byte or similar means crashes are not revealed until possibly production if your unit tests didn't get that oneeeee edge case right.

If I'm going to do a new project in the future, I will demand it will be a statically typed language. I'm sick of dynamic languages.