The sad truth is that websites, like travel policies, are generally not designed and created by the people who use them most.
I once sat in a fascinating user monitoring session we did for a website I ran and several times the entire team watching uttered the words "but why would they use it like that?" ... I kept having to say "it doesn't matter why - it matters that they do and we should make that process better".
But those sessions were expensive and we were only allowed to run them on major revisions.
And it didn't help a few of the people the agency found for us had lied for their money - including claiming to be years old customers who'd registered on the website the night before the session.