Pry debugger is great when or if it works. On windows this is generally impossible, even on Ubuntu it is spotty. Debuggers for other languages just work.

Then there is also a ton of tools Avdi didn't touch on like silent failures from gem, that bundler is not installed by default, that editing code at runtime damages what kinds of inspection can be done, many gems are platform specific, how underspecified Ruby is and in general I find few things can be relied on.

In other languages I find that what I can rely is much larger than in Ruby.

If it didn't pay so well I would have dropped Ruby a long time ago because the language is composed of so many half measures.