I've done the following, but I'm sure there are many methods: From file manager, select choose file or multiple upload (if they are of the same year) to select the images to upload. When uploaded, you'll notice a tab that says "Sets"... under that tab you can add them to an existing set or create a new one they will belong to. Save.
Using a gallery, like Gallerific for example (I don't remember off the top of my head for others), you can choose to display a custom gallery by selecting one pic at a time or display a set > choose set and select the year/set for that gallery and all will display for that year... Add a new gallery block etc. repeat as necessary

PS If you've already uploaded images, they can still be added to sets in the file manager.

PPS. Images can belong to more than one set and you should be able to sort order within a set if memory serves me right

Adrian