I wouldn't upgrade the BWI-DFW, DFW-BWI portion from the beginning. Miles and co-pay will allow you to upgrade up to 3 segments so you might be better waitlisting for the DFW-OGG-DFW portion to clear and then add the BWI. Granted, this will cost $700 and 60k miles if all goes through. It is your call. If you have the miles, enjoy them as you which. On the flipside, those 60k miles can be used for a coach saver fare to Europe, which is 40k, just a thought.