Growing up the word meant "deprivation", "hard living" - my grandmother and father lived for two years in a 12 by 12 foot hole in the ground with his brother. They worked long hours to "break" the ground. All four grandparents were already second or third generation residents on Turtle Island; and moved West to the prairies following the promise of the federal government in 1880. They were not really adventurers although perhaps the Dewar side was moving away from a family that disapproved of the marriage. The Ward side simply had too many children and someone had to move out.
My father and his sister became a little aware of racism in the 1950's. Dad found out that the hired men could only cash their cheques through the Indian Agent; he was extremely annoyed because he really disliked the "drunk swaggart" - it was bad enough, he thought, to have to go through the agent to hire the guys in the first place! His sister and brother-in-law were undergoing the stirrings of awareness as well.
Awareness moves onto the next generation, amplified.
"Homestead" however antedates North America. It comes from an old English (some argue Scottish) word, "hâmstede", used before the year 1000 CE. "Hâmstedes" were owned by people who were not well off and often struggled for their sustenance - but could call a place that included a lot of land out outbuildings their own. This distinguished them from peasants. As British common law transitioned into a formal legal system, the "homestead" was often exempt from forced sale.
Bill Curry, my partner, was of the first generation born in North America on both sides of his family. In 1985, the Curry/Dewar's visited his Curry relatives in Ireland. We discovered that they considered themselves living on a homestead acquired in the 1680's. Their ancestors were Scots that moved to Ireland across the Irish Sea. From the 1680's through the 1700's, Scottish peasants were unhappy with opportunities in Scotland and formed the Scottish diaspora to Australia, North America and many other places. It is rumoured that some men and women even committed minor crimes so that they would be jailed and then shipped to "the colonies" at the government's expense! Later, in the 1700's, big land owners in Scotland, usually various nobles, "cleared the lands of peasants" so that great herds of sheep for wool could be raised to feed the newly industrialized fabric industry; the largest Scottish invasion of North America occurred at this time..
(Experiencing the "clearances" might explain why so many Scots became allied with First Nations. It does not explain John A MacDonald, a lawyer that rose beyond his level of competence He drank heavily and many of his decisions were controversial in their day - including the execution of Louis Riel and the starving of the Cree in what is now the North Battleford area. That he rose to prominence is a warning to those who think that our "democratic" process is failsafe. That we can weed out sociopaths - they are often great manipulators and brilliant charmers - or outright psychopaths who lack empathy and promote violent solutions at every opportunity.)
The word "homestead" moved across the Atlantic and came to mean "a lot (quantity) of land adequate for the maintenance of a family". Not specified but understood was that only white men and families need apply. No one with black, yellow or red skin could apply. Furthermore, the 160 acres could only be "developed" using rather strict European farmer/peasant cultural expectations. In 1872, the word "homesteader" was first used.
The notorious "Homestead Act" in the United States was signed into law by Abraham Lincoln in 1862. Almost ten years later, Canada in 1871, "negotiated" Treaties 1 and 2 with First Nations. This made way for the "Dominion Land Act" in 1972. The provisions of the treaties were never fulfilled; the federal finances did not have enough money to fulfill the financial agreement. John A then proceeded to solve the "Indian problem" by eliminating the people themselves. He became renowned for bringing about his vision of a country sea-to-sea. He was a drunken sot will delusions of grandeur.