I think there is something compelling about the combination of a shallow initial learning curve and optional elements like static typing that can improve maintainability for more complex projects. The shallow learning curve makes it easy to get started, then once basic familiarity has been established, one can move on to code that isn't as 'clean'.

'Optional' is key there. Don't want to use type checking? You don't have to.

It's a bit like how some video games introduce one skill or gameplay mechanic at a time, which helps keep players from being overwhelmed by new concepts.