I actually did , and yes it's extremely challenging and can be rather rage inducing; "it doesn't work" --> what doesn't work --> "the thing" --> what thing --> ∞ ...

But the thing is conversations like the above ie. both external support and internal feature requests could theoretically be handled by a GPT-like system also ending up in a ai created custom specification that could both be implemented and documented by the ai system instead of humans?

I know we're a few versions out, but still.

If just being persistent and willing to iterate solves the issue, then yes, GPT-like systems could do that. If you have to employ creative thinking to even find out what the customer wants, then check it in the system, debug some processes and derive the desired feature or correction, then we are very far from having such a tool, IMHO.