Had a great chat with the Ticket Center reps at Disney Springs when we arrived. Updating the thread in case anyone needs it for future reference. As I shared, I am working with 2 sets of current tickets that could be upgraded to an annual AP when it opens for out of state folks next week. The military tickets could be upgraded but they recommended against this option since the first ticket was used in January. As someone mentioned earlier, the AP renewal back dates to the first date of use. The military tickets can be used anytime within a year, so we used 2 in January for MW weekend, 1 this weekend for Springtime Suprise, and the last 2 will be used in November for Wine & Dine. Upgrading would connect my AP to January for renewal.
The 2 day tickets I'm using this weekend (because of blackout dates) would need to be extended to 5 day tickets. This would allow me to use them this weekend and call in on April 20 to upgrade to apply the purchase cost to an AP that renews in April. Essentially, I'd be paying for half of the AP now for the ticket extension and then the other half next week when the AP opens.
The final option was to just purchase a new AP and use the voucher within the year and choose when would be the best time to activate and not link it to any current tickets we hold. We have trips planned for November and next January already. I'm leaning toward this option just to have more flexibility. Our travel plans between May-August are pretty much set so I don't anticipate us being able to come to FL before Sept. Seems silly to upgrade now and then not use the passes again until September or possibly even November since I could not come in October.