my current expiration is Oct 26, a week shy of the date WN wants to status match for. So it looks like I will be able to have enough flights by Oct 22, 4 days shy of my expiration to qualify for Elite next year.
If you re-qualify for Elite on October 22 your Elite status should be automatically extended to October 26, 2015. Then as I understand it by November 1 you should get A-list for all of 2015.
Do you currently have A-List status goes to the end of this year?
In any event you will have a good argument if Southwest doesn't do it automatically.