The convention of 1883 was the first in which Cheshire had taken a significant part, but from that time forward his influence and counsel became increasingly important. He was made chairman of the committee on the division of diocesan properties. His committee had a difficult task in dividing the permanent funds of the church to the satisfaction of both dioceses. The problem caused a few very bitter discussions in several succeeding conventions. Cheshire usually led the discussions, often taking the side of the new diocese against Bishop Lyman and a majority in the convention. More often than not he won his point, since his opponents rarely took the pains to make themselves fully acquainted with the facts. Cheshire was sometimes accused of being discourteous in his manner towards the Bishop when they disagreed. It can be fairly said, however, that he was never intentionally so. In a letter to the Bishop he remarked that he often spoke excitedly and impetuously upon any subject about which he felt very strongly, and that this characteristic was sometimes interpreted as discourtesy.[20] Cheshire had the highest respect for Bishop Lyman and admired him both as a bishop and a man. Nevertheless, it was almost inevitable that two such decided and forthright characters as Lyman and Cheshire should have pronounced disagreements. One of Cheshire's most valuable contributions to the diocesan conventions was his services on the Committee on Canons. He was a member of this committee from 1884 through 1893, with the exception of 1887-88, serving as its chairman for several years. He made himself thoroughly acquainted with the canons of the church, and while serving on the committee, he did most of its work. During these years debates on the canons occupied much of the time of the annual conventions. Long after becoming bishop, Cheshire remarked that he was happy to observe that this was no longer true, and that "We have come to be interested in more important business." He did not mean to belittle the value of canonical law, but rather to emphasize the importance of other work.