That is a big area to maintain in turf! The problem with ‘rolling’ is not damage to the grass but damage to the soil by compacting which then damages the growing turf. If rolling seems to be the only option, I would try it on a portion of the turf and see what the results are, if it really does even out the ground or not and also whether or not the grass stays healthy. Another option would be to get a yard of garden soil delivered and begin filling in some of the more major dips. This is not going to be an easy, quick fix with any method. You could also consult with a landscaping business in your area for any ideas they could offer. Perhaps you could consider adding some native shrubs and plants to reduce your grassy area. And I certainly understand your desire to make the mowing process easier on you. Good luck!
Thanks for the response.