It turned out there was not a secret combination of search sites or dropping someone's name when calling the airline directly that would work. There is in fact only one true way to get the lowest possible booking price. BOOK FAR IN ADVANCE. Between 90 days and 150 days to be more precise. BOOK NOW! As of this post, NOW is the best time to grab deals on flights for the 2015 holiday season.
****Here is a link for Booking.com. I used CheapOair and there is a link for them below****
With my plan set, I used CheapOair to book my flights, and managed to get the airline, times, and seats I wanted. While the cost per ticket still ended up being around $500 I could have easily spent $700 if I had bought flights in October or November.
So now if you can make your plans and get your flights booked, you can take your savings and splurge for one of the upgrades, like a hotel package or a rental car. Or you can use the money for a nice meal out on vacation or some extra Santa swag. The point is that dough is yours because you took advantage of foresight and planned ahead. Now if I can just plan to handle the laundry I might be closer to winning this "adulting" game.