I wonder how a more competent form of Siri/Alexa/Home might change these market economics. If we ever come to rely on digital assistants for much more than the weather and turning on our lights, the problem of remembering goes away.
"Hey Siri, book me a flight to Vancouver for next January when prices are below $400"
I've been ideating on a travel planner for a while, and one of my original ideas was actually along these lines. I figured I'd have to build out a full travel planner first, but then I found this (https://www.inspirock.com/) which kinda covers the planning part, and probably wouldn't be toooooo difficult to hook into a voice command
"Hey Siri, book me a flight to Vancouver for next January when prices are below $400"
"Hey Siri, show me my travel itinerary"