Overall, the Master Rollover is a very helpful tool that saves a lot of time, but it fails to do so with the gradebook rollover. As it currently is, an error comes up if you try to rollover last year's gradebook into the new current year due to the fact that the dates don't line up, which is the case every year since the exact dates always shift. The official suggestions for working around this are either to adjust the previous year's dates to the current year (or vice versa) so that the rollover can be completed, or to manually input all the gradebook info for the new year. While the former is the quicker of the two options, it is still a laborious task, and additionally creates inaccurate information for the previous year (unless you were to go back and reset it all after the rollover, which adds further time to the task). It seems there should be a way to complete a rollover for everything except the dates, which would save a significant amount of time.
RESOLVED - EDIT: currently, matching the dates is actually not working.