Craft Question: Backstory and Flashbacks in Novels

I'm reading Jeffrey Eugenides's Middlesex. If you know it, you can guess why I am thinking about backstory and flashbacks. If you have not, it is a novel about a Greek hermaphrodite coming of age in industrial Detroit. Its plotting is an eccentric web of history and characters, and evokes shades of John Irving.

Most of all, the first half of its 500-plus pages is family history, and I want to know how this hippopotamus of a tome manages to dance so lightly, so entertainingly, across fifty years of history and two continents with barely a nod to its hermaphroditic narrator.

The first-person narrator adds cohesiveness, yes. The lustful lead-up to an intermarriage between brother and sister is relevant, too, yes. Yet the tantalizing hints of the original hook—the mini-scenes in present-day Berlin, the narrator's scant mention of his memories—are enough to lure us ahead but not leave us frustrated.

The struggle to insert backstory (and especially flashbacks) is an immense part of a writer's task. It means you have to interrupt the escalation of tension in a story, and shift back to something that already happened; you have to stop the story clock. You have to reassure the reader that history is more important, for a moment, than the story at hand; you have to convince her that the story at hand will be somehow incomplete and unsatisfying on its own, and urgently needs the voice of history to fill its empty spaces.

And usually, the attempt fails.

Are you a writer? Do you have a talent for moving your narrator through time? What do you pay attention to when plotting these scenes, and how do you know that the shift works?

Caffeinated spiders weave tangled webs. Maybe backstory would be a non-issue if I quit coffee.