All very helpful. In 2008, we took this same trip (flying into Sydney...with a jump over to NZ) and I don't recall this being so difficult! Booked the flight and got the upgrade all in one booking. I would agree that the odds are getting worse. I have enough miles banked to book us both in business using a standard award....starting to think it may be worth it. Though I would prefer to spend a couple dollars to (1) get more miles from the flight (2) have more miles leftover for more trips!
I am going to keep researching...next decision will be do I book the hotels not knowing when I will be flying!
Thank goodness I don't have a full-time job and other things going on in my life. Oh wait....
