I suppose it is possible that Robert Hudgeon went off to Canada, leaving Olive in England with her daughter Margaret, and then married a second Catherine.

Olive lists herself married in 1911 England census, and then a widow in 1920 and 1930 (both in Dodgeville, Wisconsin). I have seen other instances where the woman identified herself as widowed when, in fact, she was divorced.

However, another possibility is that there were two Roberts, and Olive's Robert died, perhaps in England.

Do you have the James Hudgeon who married Margaret Cowley, daughter of John Cowley and Margaret Skillicorn? James and Margaret's son buried at Lonan: Lonan MI-B26. “Sacred to the memory of Paul James son of James Hutchin and Margaret Cowley his wife of Gretch-Voar who departed this life the 29th of August 1851 aged 3 months.” It would seem this James must be related to the Robert who has connections with John Cowley in Wisconsin.

Also an Ida Kermode who married Will Cowley, son of John Cowley, Jr., and Jane Kneale (John Cowley, Jr., is the one who "brought" Olive Hudgeon and Margaret Qualtrough to the United States in 1914, to care for him after his wife Jane died.)