I primarily use ruby, and I agree it doesn't have to be unmaintainable, but I also think that static typing will eventually win because it's easier to make type systems more powerful and expressive than it is to make programmers smarter or able to fit a larger system in their heads.

One reason dynamic typing has so much mindshare is because the comparison was always against Java which not only has some of the most boilerplate, but can't even prevent a null pointer exception. So in effect Java is 50% safer at 5x the cost of well designed Python program. However a language like Haskell actually brings real value from the type system (among other things), so you get more like 5x the maintainability at 50% the cost.

Obviously those are just made up numbers, and we can debate the particulars of Haskell vs other modern type systems, but it seems clear to me that is the richest soil for future gains in software maintainability and correctness.