Yes, it seems like every generation has this debate again. In the 1980s people realized how horrible it was to maintain complex software and type checking was seen as a fantastic innovation — there would be no going back. But today we are still having this debate.
Richard Pringle’s response makes a good point though, that perhaps it is not an either-or situation, and that there might be a new approach that carries the advantages of typing but in a more flexible way. Aspect oriented syntax is an example of another approach.
But I agree, that languages like Python and Ruby are a nightmare to maintain or use other’s code, but one can quickly write a-lot of code that only you understand!