By the time of his death, Appleby owned at least six messuages, a windmill and a ‘place’ in Lincoln and its suburbs, being by then one of the richest merchants in the city. His wealth seems to have come largely from the wool trade, although he evidently had some connexion with the leather-sellers of Lincoln, to whom he left five marks for the purchase of a pipe of wine to be consumed by them after his death. He is first mentioned in May 1396, when the merchant, Robert Messingham, made him one of his executors. This task brought Appleby and his associates into conflict with the ecclesiastical authorities, and at some point over the next four years they were excommunicated for contumacy by the bishop of Lincoln. They duly appealed both to the papal see and the court of Canterbury, and in July 1400 they were bound over in sums of £40 to answer the bishop in the secular courts where he had challenged their right to a stay of execution.
Meanwhile, in September 1396, Appleby was made bailiff of Lincoln, and thus became responsible for holding the election to the first Parliament of 1397, to which he himself was returned. In the following June he obtained royal letters of exemption from holding any further municipal office or government appointment, but since he went on to become a royal commissioner and j.p. (as well as serving a term as mayor of Lincoln) we must assume that he had no real desire to avoid such commitments. One year later a royal pardon was awarded to him as ‘merchant, alias wool merchant of Lincoln’; and, given his current involvement in the cloth trade as well, it seems that his commercial activities were indeed diverse. Appleby was one of the leading citizens, who, in 1398, witnessed a deed for the mayor and corporation of Lincoln. Further evidence of his social status may be found in the papal indult which he received a few months later permitting him to make use of a portable altar.
Appleby drew up his will on 1 Apr. 1407 and died before the end of the month. The date of his marriage to the twice-widowed Joan Saltby is not recorded, but since both of her former husbands had been prominent members of the mercantile community she must have made a substantial contribution to his finances. She was left a life interest in all of his property save a single messuage in the parish of St. Peter at Arches. This he settled upon his ‘dear friend’ Alice, who also received a bequest of £100. He left additional legacies well in excess of £130, his only surviving relative being his sister, Alice, the wife of Robert Ratheby. Joan Appleby did not long outlive her last husband. She died in, or shortly before, February 1409 and was buried beside him in the church of St. Benedict, Lincoln. She too left generous bequests of plate, jewellery and cash (alone worth over £71) and appointed her son, Peter Saltby, a prosperous woolman, to be her executor. Joan was the godmother of William Dalderby’s two sons (or young kinsmen), who, along, with Dalderby’s wife, were beneficiaries of her will.