I'm thinking also of one set of great-great grandparents. He was from a very poor farming family, who had decided to look for work in the city instead of emigrating to the US. She was from a considerably wealthier farming family (which owned their own farm, his didn't), and also had decided to move to the city, probably more out of a desire to see the world (and the wonders of fin de siecle city life) than necessity. They did well for themselves in the city, but in their old age they moved to a rural cottage near the farm she grew up on. (I think actually she inherited the land, and considerably more, but that they sold off the rest).
I think that with money, cottage core can be a desirable life. A big part of the reason life was hard for life-on-the-prairie people was that they had debts, and need for a good deal of things they couldn't grow themselves. With a little money, like both my great-great grandparents and the stereotypical Beatles retirees had, cottage life can be fine.