"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.
Don't know if this is covered in the help pages (it certainly should be on the link about search results, if not the others):
Because editing the order of a list can be cumbersome, given your 1st goal, I would sort the list using the Sort feature. If you really want the list in that order permanently, and have not yet added comments to any titles, my favorite method is to, while the titles are sorted and in compact view, add them to my Watchlist using the + in the bookmark symbol (or on the poster in detail view.) Then empty out the destination list, and move the titles from the Watchlist to the destination. Note: this method loses the date added to the destination originally, in case that's important to you.
Of course, I keep my Watchlist very trim, because it is the only tool for doing what I just described.