Not OP, but hopefully this helps with your first point: we're happily using Sorbet with Rails (leveraging sorbet-rails). It's by no means perfect, but a gradual typing experience in Ruby never will be, unless you restrict the way you use the language. The benefits of having at least some level of type-checking outweigh the cons, IMHO. Sorbet picks up many of the little typos that only become apparent when you try out the code / run a test. I've been using an unofficial VS Code extension for ages, and I really like the increase in iteration speed.
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