"1: How do organize titles on lists by year? Like, oldest to newest?" This way: How can I move/rearrange the order of list items? To make it easier, you may open two tabs of the same list: one where the list is ordered by year, and another where this list is in edit regime. But if you compiling a new list, it's better just to order the titles by year and then add them one by one to the list.