Do not miss that one will find all of the language's pain points. I'd wager that a dynamically typed languages such as Python has quit a few more pain points at scale than a more principled language such as OCaml.

I love Python's bignum arithmetic when I write small prototypes for public key cryptography. I love Python's extensive standard library when I'm scrapping a couple web pages for easier local reading. But I would never willingly chose it for anything bigger than a few hundred lines. I'm simply not capable of dealing with large dynamically typed programs.

Now if people try Rust or OCaml with the mentality of an early startup's Lisp developer, they're going to get hurt right away ("fighting the language" and "pleasing the compiler" is neither pleasing nor productive), and they're going to get hurt in the long run (once you've worked around the language's annoying checks, you won't reap as much benefit).

If you'll allow the caricature, don't force Coq down Alan Kay's throat, and don't torture Edsger Dijkstra with TCL.

Though OCaml’s tooling pain points hurt at least as much as Pythons, even though I adore the language.

This is somewhat true - scaling is hard no matter what - but some things scale much better than others. I have been miserable working with ruby on rails codebases that are much smaller than java codebases I have been content working on. This is despite personally enjoying the ruby language far more than the java language.