Right now, I think my most watched is Kuragehime at 3x. Some shows I've watched twice: Love Live! (both series), Ghost Hunt, all of the Monogatari series (up to Owarimonogatari, which I've only watched once since it's just coming out), White Album 2nd season, and Mahouka Koukou no Rettousei.
That's not including movies, I guess. You'd have to throw Ghost in the Shell, Garden of Words, 5 Centimeters per Second, and pretty much all of Studio Ghibli's stuff on there. If I love something, I tend to watch it at least twice.