My major banes are:

* performance. You have a hard job retrofitting performance to Python

* typos. Typos that survive my Integration Tests which can never have enough coverage. Stuff that just won't compile in a static language becomes a runtime issue on a dynamic language, and they can hide for months outside the happy path e.g. in some error handing code

* poor libraries. I get nice warm happy feelings about various async server frameworks that last until I have to debug them and stare at their innards and realised they were contributed to and diluted by twits

* pip/virtualenv doing a poor job with native code in modules

At least it has namespaces / modules and such

At least its not common for every 3rd party lib to want to squat on a function called $

And so on.

Static typing is a major plus when you are beyond the prototyping stage and heading heading towards the release and maintenance phase.

Which is why I'm on the look out for implicitly strongly statically typed languages that look like Python :)