I have this problem every year. Last year I went on a 6 week vacation. I wanted to go to an African safari, but where? What should I see? What route is best? Turns out safaris are super-expensive and I can only afford 2 weeks. What should I do for the rest of the time? My flight had a stop-over in Turkey, so I might as well spend a few weeks there. Should I also go to Greece, Croatia, or southern Italy? It was October so I only want to go where the weather is still warm. I wanted to stay in interesting B&Bs, go hiking in Crete, see gorillas in Uganda, etc.
I ended up going through a human travel agent who planned a wonderful trip at a steep discount to the luxury safari pre-planned trips because she understood what we wanted to pay for (experiences) and what we didn't care about (fancy hotels).
Not many people go on six week vacations, right? If you were planning a two week holiday, would you still be faced with so many decisions and complexity? If not, the market you represent would be limited to longer holidays, which may be a very small market.
Second, could an app provide you with a better service than your travel agent? i.e. is this a "problem", or is a "solved problem" because a satisfactory solution exists already?
I usually take 2 to 3 week vacations, but I try to do interesting things. Ride horses around mongolia. Hike volcanos in Indonesia. Bike and eat across France. Planning is a huge pain because we have to learn everything before we can make the right choices. A travel agent already knows the domain. I do think there could be tools to help agents arrange trips more quickly given our unique constraints. Sadly, there is no app for that. Regardless, the market is likely a small niche.
I ended up going through a human travel agent who planned a wonderful trip at a steep discount to the luxury safari pre-planned trips because she understood what we wanted to pay for (experiences) and what we didn't care about (fancy hotels).