Honestly? The “am I making the right decision?” part. Not just finding flights or hotels but confidence. Reassurance that the timing, destination, and plan actually make sense for me, not just on paper.

@Steven Davenport yes basically if AI could actually reassure me that my choice in trip is actually right for my situation. Which involves things like timing where you're going the weather the plan actually makes sense. LOL that's about at the line where it's almost able to understand human psychology and issues beyond just being able to work out the logic. I imagine one day it will get there