This suggests to me you've not spent much time with Pry. Are you aware of this:
https://github.com/pry/pry/wiki/Editor-integration
It's not perfect - doing it perfect with Ruby is a hard problem, as a method can have been defined and redefined in multiple places. But it works very well.
It's still just reloading a file. That's not what I want.
Why do you think you need more?
Because I have access to something much better any time I write Scheme.
So far, from what you've pointed at, you seem to have picked the most restrictive simplistic examples of what Pry is capable of as a counter-example to explain why it isn't enough for you, rather than explain what it is you believe is actually missing.
Point is: You have access to much better than the examples you've pointed at with Pry as well.
It really isn't that simple, though, and I've only used it for the most trivial of situations.