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Ann, born 1869, was the daughter of cottars Angus MacAskill and Ann MacDonald of Port nan Long. By 1891 she was working as an assistant teacher, living at the home of her maternal grandparents in Borve, Berneray - grieve Neil MacDonald and his wife Christina. The site of their home was later known as Tobhta Nèill ‘ic Lachlainn.
As an assistant teacher, Ann would have been working at Berneray School, where her aunt’s husband, Donald Johnson, was schoolmaster. Ann, who remained unmarried, later moved to Obbe.