I need a little help with the creative thinking and, while it's not a US-specific question, figured I might as well start with the brains in this forum before looking elsewhere. We've booked YVR-SYD (stopover)-AKL-YVR using US miles and traveling in J on a mix of AC and NZ and I'm having a hard time sorting out the positioning flight. I need to be in Vancouver somewhere between June 4-6 (preferrably the 5th) and returning June 21. Can't return June 20; might be able to do the 22nd but an extra missed day's work for my fella comes at a substantial price (missed work = missed pay). I really, really do not want to sit in Y on the positioning flights because, while the outbound would be tolerable, a combined 8+ hour travel day in Y after a 15-hour transpac the day before makes me want to cry already. I could: -DCA-YYZ-YVR on AC for about $3600 for 2 in J (yeowch) or about $1600 for the two of us in Y -DCA-PHX-YVR on US for about $1800 for 2 in Y; if I take this path I would use my Mastercard companion cert to get that price down to about $1000 for the two of us -Would consider upgrading the US itin on miles but TBH it would be 60k r/t for the two of us which puts me off a little bit--- that's more than we spent for an Envoy low award to Europe-- plus the US itin has a 7:00 am departure on the outbound and a 7:45 am departure on the return; I have a real problem with such an early return coming back after a transpac -Could also do the AC DCA-YYZ-YVR for 100k miles for the both of us but again, now that I am used to 100k miles getting me almost to Australia in J, a little part of me weeps to think of using tthose to go to Canada (even if it is really far away in Canada). -I can't find enough NF availability on UA metal to try a "dummy" booking to see what their upgrade upsell offer is; good NF availability DCA-ORD but either 0 or 1 ORD-YVR/YVR-ORD across the board (NF is the UA upgrade bucket from Coach to First and chances are, if you book when there is NF available, they will offer you a cheap upgrade. Since I've seen them as low as $225 each way transcon, and they convert to an A booking at 150% PQM, I like this option, although they can frequently be very overpriced) -Buying a Y fare on AC and upgrading with miles will cost more than buying the J ticket outright -I have considered canceling the whole itinerary and starting over with the WAS-xxx-YVR included; while this is definitely the cheapest option, a 3-stop itinerary and a 29-hour travel day puts me off, plus there are just too many chances for something to go wrong and leave me somewhere other than YVR when my flight to SYD takes off. I'd rather spend a day or two in each direction in Vancouver (lovely city btw), have the easier travel days and the cushion against WX/MX messing things up for the transpac -I've also considered rebooking WAS-YVR (stop)-SYD-YVR-WAS and using miles or $ to go between SYD and AKL but as I understand it, I only get one stopover so I would still have a 25-29 hour travel day in one direction or the other -I could also suck it up, buy the US tickets and keep my fingers crossed for the comp upgrade -I do not want to fly in/out of SEA and take the train or commuter jet to YVR, it's just one more moving part that can break and one more thing that makes the journey longer. If I could get the AC fare down by about 25% I would probably just book the J ticket outright; it has the best itinerary in terms of time, and the return from YVR-YYZ would be on their A333 with International config so I see good value on that. But none of the recent AC promos are a good fit. I would love advice/input/recommendations/crafty solutions. Whatever we do, it must earn miles on US unless we pay for the whole thing on miles, and factors are in this order of importance: price, comfort, not getting up at 4am for a 7am flight. thanks in advance!