I also worry that if we hit new Clojure devs with a wall of tooling issues like this, they won't stick around, even if we tell them the underlying theory of their tooling is more sound.

This sounds like a educational problem rather than "lets dumb down our tools to cater to new developers".

Clojure seems to balance "cater to professionals VS being easy to get started with" to the first mentioned segment, something I myself has no problem with.