From what airport are you departing? If it is ONT/LAX/SNA area per your profile, are your positioning flights also in Business? If so, AC offers a 787 with lie flats to YYZ.
If it is just economy on the first flight and you are coming from So. Cal, i would stick with the PDX connection. Get row 1 (although I think the refurbished 764s all have the bigger footwells)