More thoughts incoming but it seems really strange how travel (especially spontaneous) is so tedious to plan. While the internet brought sites like expedia, kayak, and hotels.com, its really difficult to optimize against a plan. Sure you can find the cheapest hotel in 20 mile radius from the city center, but it’s on the opposite side of town far away from an airport etc. Flights are another challenge too, different factors go into pricing and prices can fluctuate significantly from day-to-day, there needs to be analysis over wider options to truly get an optimal trip. As an anecdote, some family is traveling international they spent at least 3-4 hours just trying to book flights without spending a fortune. We recently took a spontaneous road trip to SantaBarbara. Because of deltopia week, it was really hard to get a hotel room, especially with a dog. While expected, there was a lot of conflicting information online, forcing us to call multiple hotels independently: this is easily handled by an agent.