Don't forget the Two Step
Before November 1 you can extend Standard Awards and Credits by transferring them between systems. 16 Airtran credits = 2 Standard Award flights with one year expiration from the date of creation of the Standard Award.
Old Standard Awards can be "refreshed" by moving them to Airtran Credits and back.
It is also possible if you have one Standard Award Flight and only 8 Airtran credits to transfer the Award Flight to Airtran then transfer the resulting 16 total credits back to Southwest creating new Standard Award Flights with new expiration dates. With a single (or partial credit) you can "top off" the RR Credits creating a new Standard Award which could be transferred to Airtran, if necessary to extend Airtran Credits by creating a Standard Award.
As to how many Standard Awards you can use, keep in mind that you can use them when you have normal flights and the current indication from recent schedule extensions is that Southwest is raising fares significantly across the board. If this is correct then Standard Awards will be a bargain in many situation, unless Southwest cuts availability.
I kind of expect them to retire Standard Awards sometime in 2015 by a one time conversion to points, but that's merely speculation. They could just wait for all of them to be used or expire which should happen not later than November 2016.