To work you'll need a work permit, apparently pretty straightforward to receive for Americans, but you need a guaranteed offer for a job in Canada. My university, Waterloo, gets a fair amount of US international students, and I've heard there's a fair amount of Americans at top Canadian schools, so if you are looking to pursue further education, studying here is best if you plan to stay here. Another route is to study in the states but find a job here, a top American school (Ivy League/Public Ivy) will carry weight here for employment, but otherwise you're better off with a Canadian school. Canada has a rep for caring about valuing Canadian education/experience over that of any other country. US -> Canada otherwise isn't that messy of a move afaik, a lot of people move in both directions, met many Americans here, met many Canadians down there.