IMO the biggest problem with Ruby is still the docs. When you look at https://www.ruby-lang.org/en/documentation, you see a bunch of books - some of which are considerably out of date by now - and the official "API docs". For some mysterious reason, all the actual language features are also listed under API: https://docs.ruby-lang.org/en/3.3/syntax_rdoc.html. Worse yet, there's no proper table of contents - you get a kind of index on the left, but it's alphabetically sorted, and things on the same level are often unrelated. Compare to Python, where you have https://docs.python.org/3/reference/index.html that one can just read in order and end up with a very good understanding of the language.