I'm not too sure how it gets better, schedule wise from a chance to win games perspective? We only play Illinois, Indiana, Michigan, Rutgers and Northwestern twice. We play Maryland, Michigan State, Wisconsin, Purdue all once at home. Ohio State, Penn State, Nebraska, Iowa once on the road. It can't get much more favorable than that, can it? Sure, we can quibble about the order or some other wishes but that is a favorable Big Ten schedule.
Four top rated teams only at home. Four lesser rated teams only on the road. And the opportunity of five beatable teams twice.
It'd be nice to start with an easier beginning but kept in perspective again, we are young and the season is 18 games long so we should get better as the season progresses versus coming out of the chute with any game being a lock under any circumstances. So from that idea playing Ohio State once on the road to start the season is maybe alright.