Exactly. Places like TripAdvisor simply isn't going to cut it. I have a friend who tried to tackle the problem a couple of times but still haven't succeeded.
My guess is that the solution is something simple, something that isn't algorithmic but rather a platform for travel agents who can listen to and understand the individual needs.
sure theres plenty of hotel or airfare or rental or 'town of xyz events calendar' sites but no one solving the entire problem.
I've yet to find an end to end trip planning site, especially one that is family oriented.