The only reason I gave up resisting and started writing any significant code in Python at all was that it got some kind of type system, and thus became less unpleasant to code with.

"Pleasant to code with" does not describe getting "AttributeError: 'NoneType' object has no attribute 'foo'" 25 levels deep in a stack trace already obfuscated by dynamic object-oriented nonsense. In production, because it's an unusual case and testing missed it. Not that test cases aren't way more work than types anyway.