The only part of writing/maintaining code that I've found easier/more pleasant with dynamically typed languages is writing unit tests (due to the fact that mocking an object is as simple as just declaring a hash literal or JSON object). On the other hand, I find that I need to write extra unit tests to verify integrity that would be be verified at compile time in a strongly typed language like Java.
I would strongly recommend people check out DropWizard. It's an opinionated framework for writing Java servers that comes with a handpicked stack. It has many of the convention driven advantages of e.g. Rails but fundamentally you're still writing code in Java (or another JVM language like Kotlin).