This is surely anecdotic and very subjective, but I have (in Java and in C++; IIRC the exact versions were Java 7 and C++03), and the level of pain was lower th

This is surely anecdotic and very subjective, but I have (in Java and in C++; IIRC the exact versions were Java 7 and C++03), and the level of pain was lower than with a Python code base that was about one order of magnitude smaller. In the case of C++, the pain was mostly asociated with an ancient build system we used; the code itself was relatively manageable. There was almost zero template code, and maybe that helped (although in other occasions I've worked with smaller C++03 codebases that relied heavily on templates and I didn't find them that bad). Not all codebases are equal and maybe I was lucky, but in my experience, using dynamic languages (or, to be exact, any language where the compiler doesn't nag you when there is a potential problem) doesn't scale well.