For less frequent, bespoke travel like vacations or holidays, algorithmic assistance would be overkill and get in the way. Plus I would not necessarily want a third-party service aggregating that data about me (and selling it or driving ads with it, of course).
It’s very similar with automated calendar assistants, which I am generally skeptical of. Even if they work with human level accuracy, the times when the slightly lessened cognitive load of offloading to the assistant is better than just dealing with scheduling are too rare.
And if you’re in a high-powered business situation where scheduling is a huge volume of chatter for you, you probably already could afford to pay a human assistant to do it and cost savings to switch to a digital assistant would be round off error.
It’s why the calendar app companies market the products to everyone — as if every employee in a company needs a C-level executive treatment for calendar items — because the only way there is any money in it is to sell big enterprise licenses cover a lot of headcount, yet this is inherently antithetical to the product. Big headcount of staff, almost by definition, don’t spend appreciable time with calendar overhead. (Or else your business is in trouble.)
This would be one option I could populate other options. You could create these options for yourself and others. Ability to crowdsource itineraries.
No need to sell your data or show ads. I could make money by taking a dollar here or there when booking your flights or hotel.