For #1 - hotel and flight deals matter the most For #2 - they figure out most of the stuff while on the move and do not want to plan much. they pretty much buy to-fro tickets from their base and figure out everything else on the move.
Monetizing the idea of 'where should i go' looks pretty tough to me. My pals tried a venture wherein based on the region of interest the website would come up with an itinerary, they couldnt do well and had to fold.
Travel industry needs technology and some disruption; it hasn't seen anything 'interesting' other than the known Skyscanner, TripAdvisor, Agoda etc for a long period of time now.