I get the impression that this is a system wherein honest mistakes and failure to adhere to strict rules are punished, while outright cheating is allowed simply because it's difficult or impossible to catch. Meanwhile, the strict rules exist in part in order to try to make cheating harder, but don't actually seem to make it harder to cheat, they just make it harder to complete the trail in an honest fashion.
As such, this seems like a cautionary tale for a wide variety of human-designed systems, especially centrally-administered systems such as in governments and corporations.
That said, I love the idea of a trail like this, and I love the idea of collecting stamps along the way.