If only we had some combination of software and people with expertise in destinations. Maybe we'd call it a travel agent or something like that.

That was snarky. But it points to the historical problem here. Most travel agents didn't/don't have a lot of expertise outside of fairly narrow domains. And they mostly depended on commissions from pretty routine stuff to subsidize labor-intensive planning for oddball itineraries--which I'm guessing can't be easily codified in software.

In fact, I'm sure there are plenty of competent travel planners but they cost money--i.e. are luxury goods--and most people don't want to pay the money.