This is very nice until computer says no because of some bug and you end up with a clueless staff with very little idea about the rules because they're used to just following whatever the computer says without understanding why it says so.

This is already very common both in airline industry and beyond. Back in the manual days, staff had to spend a lot of time learning the rules, having to know them to the last obscure exception and applying them with their brain. As more and more stuff can be simply determined by software, their understanding of various less common cases deteriorates.