I lived this working for a company that, as part of a suite of services, tracked international business travelers for the companies they worked for. The air travel part was a nightmare.
You know what else was a nightmare? There's an airport in Hong Kong which technically isn't in any country as per most land country boundary maps; it's built it out in the ocean. It occasionally gave us grief when we updated map data because we'd have to go in and manually change the map boundaries so the software would correctly locate travelers at the airport as being in the country.
Which countries are Hong Kong, Macau, Tibet, and Taiwan airports in? Hong Kong has since become un-controversial, but no matter what you choose people get upset about it.
That system was so complex, it was fascinating. The fight data alone is a nightmare, but when you start factoring in itineraries, and the fact that there's no commonly used standard for booking systems and booking agencies have terrible data quality control, our most common issue was data quality; even after 15 years, the we'd still find edge cases in the system where real world varied from theory.