Well I would feel better if Cheshire answered this for you since they are the experts on all things tickets!
For the gift card offer you have to buy a certain number of days ticket, correct? What I would do is change that offer to the minimum number of days required for the package offer. I would remove the hopper option and make it a base ticket (number of days you have to buy is based on your stay), because you are paying for that out of pocket. Then I would take those base tickets and upgrade them to an annual pass because the annual pass includes the hopper. Now you are paying for the upgrades of hopper with Disney's gift card money.
No matter which day you upgrade your tickets to an AP the annual pass will be back dated to the date you first used those tickets.
So let say you go to Disney on June 1st and have a 5 day base ticket. You should use this ticket on June 1st and go to guest relations. They will take the ticket and exchange it for an annual pass and give you the value of the 5day base ticket you paid with your package and then you pay the upgrade difference with your gift cards. Your annual pass will be dated June 1 to June 1 of next year but now you have hopping options for this trip.
Just to clarify if you go to the parks and use the base passes a few more days and went to guest relations on say, June 4th and then used the tickets to upgrade to AP then the AP would STILL be dated June1 to June 1st. Am I making sense.
So the cheapest out of pocket expense for you is to make your package have a base ticket with minimum days and then on your first day of using the MYW tickets take them to GR and upgrade them to the AP with the Gift Cards.
Again I think your best bet is to have your package be the minimum ticket and then use the gift cards to upgrade to the AP's. Otherwise you are paying out of pocket the upfront costs of a nine day PH ticket $310.98 vs paying for a 5 day base 242.82 in your original purchase price. Yes the AP will still be the same cost in the end but now you have used Disney's money to pay for the full upgrade. Does this make any sense?? I hope so!
Hope that helps.