Anyway, I'm hoping that the new static typing proposals can help make Ruby's tooling better. Ruby's greatest strength is also a huge weakness, it's just so hard to tell what's happening with all the dynamism. As someone who's been back to static typing for a while, but wrote a lot of JavaScript over the past few weeks, that's the angle I've been thinking about in this area.

I haven't been able to properly articulate why I never feel the need for these tools in Ruby, yet in other languages, they feel indispensable. Human brains are amazing: you can hold two completely contradictory opinions simultaneously. (Though maybe the different context means that they're not actually contradictory, even if it feels like it)

Probably not. Keeping the language in place and focusing on tooling would make the tooling better; as others have pointed out, there are dynamic languages with better tooling.

And, its not like people who want the costs and benefits of static typing are ill-served by the current marketplace of computer languages.