During my runs for the 100% category I also had trouble trying to get the crow to recognize me starting the quest for the around the world item. From what I understand, the crow only wants to start the quest if all previous tips have been cleared. As I remember it, the 100% route can break if you get the lantern but you don't use it i.e. interact with the dark spot above the tree boss. I imagine that the crow bugs out and doesn't show the lantern tip because a chronologically later tip has already been completed.