I think you're 100% correct that you need to feel the pain that the agent is supposed to solve. It's like trying to explain to a junior the power of Rails if they've never even built a regular static HTML website. It's going to be very difficult for them to understand why things are the way they are.

I'm very allergic to "solutions just because we can". In fact, one way I use AI that may be slightly not-mainstream is that I use AI to actively pursue subtraction that I couldn't otherwise do: cutting down on all my tools I've built over the years, culling cruft: notes, scripts, comments, etc. until I'm left with a smaller footprint of stuff I know is useful.