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Even for the relatively constrained case of booking urban travel that's not 90% the same trip over and over, there's a pretty complicated interplay of price, schedule, convenience of location, quality of hotel, participation in loyalty programs, personal time, etc. etc. [ADDED: And just personal preference.]

A longtime personal assistant who has your preferences really dialed in can probably come close. But given how much I sometimes end up fussing over even my own travel, it's really hard to see virtual assistants getting there anytime soon.



> A longtime personal assistant who has your preferences really dialed in can probably come close

If they don't come close, they can safely filter out 90% ahead of time and present you a table of the remainder, saving you lots of time.

On the other hand, more likely that digital assistant was made by the booking company and is trying to upsell you with high margin items.




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