Hi Gardyloo, thanks for the quick reply. I think there are 16 segments (not counting the word "surface") and the online tool goes all the way to the payment stage with it.
Doing Milan as a separate ticket is an excellent idea! I had put the CUN hop in there just to use up the 1 dangling segment I had, but if I exclude Milan and CUN I'd have 2 segments. Might let me add California which I was intending to do as a side trip from Vancouver - will look into that right now. Thanks!