I agree. There's a complexity tradeoff with either decision.
Having worked with both approaches, there's a time and place for both. Being able to quickly dive into a codebase is not always a good thing. One thing conservative enterprise developers should like about DSLs is that they require new developers to structure their code in a way that fits the intended domain model. I've seen my fair share of code written by developers who "quickly dove in" and they almost never fit the model and end up causing a huge mess which may be unrecoverable. Conversely, if you don't trust your developers to write decent code, trusting them inside a dynamically-typed DSL is probably not a good idea either.
Having worked with both approaches, there's a time and place for both. Being able to quickly dive into a codebase is not always a good thing. One thing conservative enterprise developers should like about DSLs is that they require new developers to structure their code in a way that fits the intended domain model. I've seen my fair share of code written by developers who "quickly dove in" and they almost never fit the model and end up causing a huge mess which may be unrecoverable. Conversely, if you don't trust your developers to write decent code, trusting them inside a dynamically-typed DSL is probably not a good idea either.