I totally agree. One of the things that keeps me in Ruby land is the absolutely phenomenal debugging/repl environment provided by Pry and related gems. When I want to understand how something works, I drop a binding.pry, run the code and start digging through the stack with the Pry toolchain. I feel like this process is so important and it's the first thing I find myself missing when I work with other languages. (I suspect you can get similar debugger/repl functionality with Python's iPython, but I don't have a lot of experience with it.)