[tome]

I don't have good answers to your first two questions, since they're very open ended. I can give you my personal experience regarding the second two.

* Would Python's dynamic type system make it more suited to problems with dirtier less clear types when compared to Haskell? If you know both Haskell and Python, do you divide your potential programs into "Python programs" and "Haskell programs"?

No, I classify my potential programs into "Haskell programs". I haven't missed Python once.

* When one writes Haskell code, do they really not have to debug and test their code?

Haskell programmers still have to debug and test, but I find it somewhat easier than I've found it in other languages.