I have been working under the assumption that Herbert Stetson was playing the role of a kindly neighbor in his involvement in the affairs of Ruth P. Brooks and her son Joseph Daggett. 

Digging deeper into the Daggett family history, it turns out that Herbert—or more accurately his wife Hattie—was related to the elderly lady. They were both descendants of the Haskell family, which we previously encountered when tracing the Stetson family history back to the Mayflower. 

Herbert Stetson served as executor of the estate of Ruth P. Brooks in 1889. He distributed her stock ownership to her five grandchildren, along with other bequests, but the surprising thing is the Herbert himself and his wife Hattie Stetson were named as inheritors of the lady's property holdings in Earlville. 

It seems that the old lady's own children were predeceased, and that most of the grandchildren lived in Nebraska or Kansas. Herbert and Hattie may have helped out Mrs. Brooks in various ways, including Herbert helping to manage her finances. 

In January 1918 when Isetta Stetson married James Bennett, the event was reported not just in the Montana society news but also back in Delaware County, Iowa, where Isetta had been raised before her family moved west. 

In fact, the article in the Manchester (Iowa) Democrat is rather more informative. Presumably it is based on information the Stetsons provided for the purpose of keeping their old Iowa friends informed of family news.

Herbert Stetson resettled his family in Montana to pursue a late career shift as a store manager