I've been working with Python for years (since 2014) and typing makes the code less buggy and easier to maintain. I also would hardly call it "shoehorning", as years of design went into it.
Honestly the only people I see who really push back against it are the people who haven't bothered learning it. Once people use it for a bit, in my experience at least, they don't want to go back.
Maybe it's just because Python is just kindof a lousy language to use in the first place. I started with Java and C++, did Python for a bit and switched to Ruby and never looked back. Being forced to use Python for anything feels like a punishment.
Years of design also went into Ruby's type system, and for the people that enjoy it - be my guest - but I would never use it for my own code.