We're in a similar boat (airplane?). Besides the fact that we like Southwest, I signed DH up for one of the new credit cards so we could get the 50K reward points. That plus what we had previously means we should have 2 round trips + 1 one way covered from California (priced both rewards flights and $$ for similar dates last year) so we'll just have to book those plus pay for the last leg from SMF-MCO (or maybe Oakland, haven't decided yet).
So we're waiting impatiently for December to open up, and definitely will need those free bags flying too! That's become a very important feature ...
Really wish SW would allow us to book those flights farther out; I'd like to start looking for DH's flight from Maui to California now, even if its just pricing it (hopefully DS5 and I will be living in Cali then already).
The MVMCP sounds lovely ... we're going to be zonked/wired between the long flights and the time change so not up for much more than either T-Rex or perhaps a character dinner the night we land. I admire your fortitude in planning that!