Thank you to everyone who weighed in! I am so happy I found this forum with users who are always really helpful! I'm lucky to have such a "dilemma."

I decided to use the $800 to book at trip to Napa for President's Day weekend instead! AS has really great fares to Santa Rosa for that weekend! The temptation to upgrade will still linger though! I can upgrade at any time, as long as there is space available. It will probably float in the back of my brain until we depart, just because I know that this is my last companion pass that allows travel in F.