I was there too. You know... It was possible to write web apps in Ruby before Rails and Sinatra, although today that feels like a party trick, like writing FizzBuzz in Lambda Calculus.
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)
> Anyway, I'm hoping that the new static typing proposals can help make Ruby's tooling better.
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.