your questions regarding the game rules (improving the interpretation).

Which passage did the red hero fly through? He flew over the rocks, not through a passage – I assume he took the shortest route to break through the passage, and there were no other passages on that shortest route.

He should have flown to his starting town, to the point you marked as number 1, cleared out the Guard Towers of the Monarchs, and then moved to the Treasury. But, as I understand it, he flew to the Treasury without clearing out a single Guard Tower, which violated the rules.