As an employee at a terminal, you have a) no reason to trust some software people who may have never seen one of them steel boxes up close, b) if this works, you or your colleague gets laid off, and c) if it doesn't work, you're now stuck cleaning up the mess the computer will inevitably make for you, which is way less fun than planning things yourself.
The 5%-10% invoices being incorrect is probably on the low end, I'd probably say it's 5-10% in total invoice VALUE. Because of the sheer amount of containers, you need automated invoice calculation. But if you miss an edge case ("We are allowed to invoice a 5 buck surcharge if the container is filled with at least 100kg of explosive goods, AND was loaded during the night shift because dangerous goods handling requirements now require us to have a safety officer on call, which we normally don't have during the night shift") you are leaving serious amounts of money uninvoiced, and you will never know. One of the reasons not that much effort goes into optimization algorithms is that there is so much low hanging fruit left on getting your invoices out correctly...
Also d.) It works sometimes so you get forced to use it and then it gets ransomwared and you're completely unable to work because they laid off so many people you can't fall back to manual operations.
You're also right about the complications and the need to be adaptable to various situations that arise. Some of that just comes from people who are afraid of getting their hands dirty and really understanding the domain they're working on. Operations Researchers and Industrial Engineers are not much different from Computer Scientists: sometimes the desire for a beautiful and simple solution prevents you from building something useful. Sometimes in order to build something useful, your idealized fast-converging LP turns into a QP/MIP bastardized rat king that only converges on an optimal solution half the time, but still gets a better-than-before solution the rest of the time. And some of us really hate that it has to be that way. The rest of us laugh their way to the bank.
- German engineers balked at tightening features on pre-production vehicles because it would prevent their use for recreational purposes - Billions were spent in overtime in a healthcare setting, seemed trivial to improve scheduling to reduce overtime, but there were numerous union constraints and simply not enough hiring supply
I wonder how realistic this google solution is (Houthi missile constraints?). In my experience it's often more valuable to develop solutions that can easily adjust to unplanned changes rather than provably optimal ones