I've started working on a time line for my son, who might one day also have problems keeping up with random history numerical markers. Dates I detested, so easy to forget, but i love history of almost all kinds. I think A big time line would help.
So this part of the time line line is about the mid century - announcing president election winner, the kids change with the time period, the markers also keep the timeline with a beat every 4 year years another marker even if president says the same.