Python was easiest, since it took couple of days to master fundamentals and I was writing good code in no time.
Also anyone working on Typescript equivalent for ruby?
RBS (descs) + Steep (type checker) is a bit younger but I found it more usable in general, especially on the corner cases.
Beyond that, it's too intrusive in the code for me. I could live with 'sig' blocks above methods, but there's an immediate readability cost when you start having to wrap stuff in T.let, T.must, T.nilable, etc.
Personally I'd rather improve my testing skills here too. Knowing how to write a good test is a valuable skill.
Some syntax is a bit quirky (blocks in particular) but if you are solid in OOP then you soon see the beauty of the core class setup.
The primary difference to Python is that everything really is a method call on a object (even if that object is a class).
To master Ruby I would start with toy problems such as Advent of Code.
I’d suggest using metaprogramming (define_method, instance_variable_send, instance_eval, send) to implement a toy ruby-in-ruby DSL is the fastest way to figure out what different.