Fair enough, I think I am having difficulty in understanding your views because firstly I have never worked with Java, closest language I have worked with is C# and I don't particularly dislike its REPL, its nothing to write home about but I don't particularly hate it either.
Secondly the image we two have in mind of a REPL seems to be different. When I am thinking about a REPL the image I have in mind is of Jupyter Notebook and Clojure, Elixir, Idris, Haskell REPLs in Emacs. The image you have in mind seems to be a basic console, so having spent my day working in a Jupyter Notebook I sit here thinking what you mean by Python's significant whitespace being an issue(Haskell and Idris have significant whitespace too). But now I do understand your views :)
P.S. I didn't get your point about python having nominal types, duck typing seems closer to structural typing to me and mypy seems to support both, but maybe I misunderstood you. Thanks for the thought provoking discussion though :)
