Comment by mikepurvis

At least for myself, business travel remains relatively simple: go to Perk or whatever the business-supplied travel portal is, put in the dates, book whatever flight and hotel are in-policy, when I get there report to the conference/customer/whatever, and buy whatever food is available when I get hungry.

It's travel for pleasure (especially with groups) where all the complexity comes in: there's a lot more stuff to schedule, more slop in what exactly happens when, more competing preferences, more need to have multiple things on deck so you can react to changing energy levels, etc.

Not too hard to see why a lot of people just give up and book an all-inclusive where every day is the same and everyone can just "do whatever", but with better tools, maybe rolling your own vacation could be made more practical and coherent for a normal busy person to put together.

On the matter of transactions in particular, I think airlines largely solve this with 24hr no-questions refund periods. So, book your airfare, then your lodgings, and if there's some problem with the lodgings, then refund the airfare and start over.