Now, 76 years after his death, his wish will be fulfilled. Alina MacAskill Simpson, Iain's great niece, has arranged for his body to be exhumed from a grave in Western Australia and returned to his beloved Berneray, where he will be laid to rest next to his parents.
Aged 27, MacAskill left his native island of Berneray off North Uist on New Year's Day 1925, hoping to succeed as a farmer in Western Australia.
He died nine years later, the victim of drought, illness, poverty and homesickness. During that time he wrote prolifically, especially songs and poems in which he poured out his pain about being unable to return home.
Ms MacAskill Simpson, 31, began researching MacAskill's life and work after using his poetry as part of her course while she was studying Gaelic in Glasgow.
She had hoped to be able to repatriate his body last year, the 75th anniversary of his death and the Year of Homecoming, but is now on course to have it returned by April this year. The Australian authorities have granted permission for the exhumation, which is due to take place in March and Ms MacAskill Simpson has raised half the 6,000 needed.
She said she became intrigued by her great-uncle's life and set out to piece together his story.
"Through the legacy of his many published poems and songs and speaking with family members, I unravelled his unfulfilled wish to come back to the island he loved.
"It will be closure for the family and it will mean his memory will live on. My biggest concern was he would be forgotten by the next generation."
MacAskill was born in Berneray in 1898, the second son of Donald and Ann MacAskill. In 1914 he lied about his age to enlist in the Cameron Highlanders and was one of the pipers who led the 5th Camerons into action in the Battle of Loos in 1915.
From 1919 to 1923 he was a constable in the City of Glasgow Police and a prizewinning piper, before he returned to Berneray to work on his father's croft and began to write.
He was later persuaded by a government scheme to try to better himself by taking on a large farm in Western Australia. But the venture went bust during the depression and he ended up burdened by debt and working for other people in miserable conditions, before dying of kidney failure aged 35.
In 1983, Dr John MacAskill, from Fort William, Ms MacAskill Simpson's late uncle, traced the unmarked grave near Perth, Australia, and erected a headstone.
Ms MacAskill Simpson said: "When we heard the Australian authorities had agreed to the exhumation, we were delighted. I will be going to Karrakatta Cemetery in Western Australia with some other families to be there for the exhumation."
The story of Ms MacAskill Simpson's quest is being filmed for BBC Alba.