Yes, Ruby has always prioritised readability and "developer happiness" over predictability and rigour, but that doesn't mean that it necessarily encouraged incomprehensible meta-frameworks. Sinatra or similar projects show how things can be done more decently in Ruby, while still utilising its malleability in order to create a nice DSL.
When a main goal to maximize a subjective trait such as "developer happiness," you are almost certain to cause the opposite for a significant portion of your users. This is the curse of inherited ruby code.
Ruby gives incredible flexibility to individual developers writing code the way they prefer. For a large team, that can be a problem but I'm not sure that was Ruby's original target group.
