Earlier quoted context omitted.
I just don't find that personally. Having to run the code over and over again to manually check for errors or having to write unit tests to gain confidence it's working is more difficult to me than getting help from static type checking. I mean why do you think it's always going to be more difficult with static types? Because you have to write type annotations?
External data are never perfectly documented or known. You usually have huge and painful experimentation phase with parsing it. Experimenting is way easier with dynamic languages. You type less. Changing your mind has a lower cost. You don't need to think about doing the right things as much.
If you have decent type inference there isn't extra typing and any time you think you're saving with dynamic languages gets eaten up having to manually fix things when errors happen at runtime. I'd much rather spend time fixing predictable compile time errors than unpredictable runtime errors.