Your Country, My Country: A Unified History of the United States and Canada, by Robert BothwellRead about another entry on the list.
There are many, many books that you can read on Canadian history; some of them lengthy tomes, others shorter and more accessible. This might be a better starting place, however. Bothwell looks at the origins of both countries and the shared history of British colonization that has shaped much of North America. Beyond history, Bothwell talks about the political and cultural differences between the two nations in modern times, and the ways in which we’ve shaped each other’s histories, whether marching in step or acting in opposition. The story of the inter-relatedness of the two countries might serve as the perfect primer for an American heading north, and might give one a better sense of whether or not the differences are significant enough and in the right places to warrant a move.