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.
Do you have an example of when Pry was being spotty? I've never had a single issue with it (on Ubuntu, too).
There are certain scenarios where you can expect Pry not to work "as expected" due to the nature of the language. If you expected it to work, it means you're just not acquainted with the tool/language. Same can be said about any tool or language, not just Pry or Ruby.
Don't know if it's still valid, but, when ruby 2 came out pry wasn't working with that. Not just that it wasn't working, it actually starts and then when I print some variable, VM crashes. I spent few hours thinking my code was wrong and finally finding out pry doesn't support the version of ruby I'm using.
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.