-> "the largest issues I've run into with Ruby typically deal with people trying to be too clever"

I agree with you about Thought-to-Code and even though I argued in favor of monkey patching earlier, the willingness to use it without discipline has raised a red flag for me and is the biggest sign of this "too cleverness" that you're referring to (at least for me). If Ruby becomes the new Java, maintaining irresponsibly monkey patched legacy systems could be a nightmare for the enterprise developer in the years to come.