I find the focus on dynamic typing a bit fascinating: you don't see people focus so much on it on a discussion about LISP. [EDIT: I meant to say that this most likely reveals something else is at work in the particular case of python].

When a C program compiles, it really does not tell you much about whether it will work or not. Maybe it is a matter of application domains, but I tend to actually spend more time testing C parts of the code compared to the python code. But, in proportion, I spend more time testing in python than in C, because I spend so much less time doing things in python than in C.

Haskell is different, because types can be used to enforced constraints in a much better fashion than C/C++/Java/etc…

The one part when simple typing systems is useful is refactoring. Doing so in a dynamically typed language is difficult (but possible, as shown by smalltalk, which is supposedly even more dynamic than python).