Originally Posted by
SAT Lawyer
If you're going to shell out this type of money effectively for the sole purpose of flying, why not B-up the whole way by flying via LAX and then onto GUM either via the one-stop through MAJ or the Island Hopper?
I've done this before in the opposite direction in a low economy fare bucket: TPE-NRT-GUM-HNL-LAX and had no problems clearing the complimentary upgrades on all eligible segments. In fact NRT-GUM still had open BF seats after all elites had cleared and 12 people or so were upgraded at the gate on the HNL-LAX segment.
If you have the time and a lower fare is available, I think you have a pretty good shot at getting complimentary upgrades on these segments. As SAT Lawyer mentioned, there is also the one-stop HNL-GUM on the way out which is upgrade-eligible, and the connection times are pretty decent.