Annual Pass, Visa, Gift Card booking help needed please!

[Cynister]

I think I've confused myself. I'm not sure which is the best way to approach this, so any help from Disney veterans out there would be much appreciated. I want to make this work to get the best deal for multiple trips. Here's the basics of what I have:
1. We have a Disney Visa card.
2. We have been saving up a bunch of Disney gift cards to pay for our next trip(s).
3. We plan on making 2 trips in 2015. The 1st will be in May for 5 days, the 2nd in December for 7-8 days. During trip #1 we will be taking another family member with us & including them in our package when we book. They will not be coming on the other trips.
4. We plan on making another trip in 2016 in May.
5. We had planned on upgrading in May 2015 to an annual pass once we got there to take advantage of the SW AP only items.

Now, with all of that said, how do I get the best deal(s)?
1. If I book the May 2015 trip with a Visa discount offer, can I use the gift cards to pay for it?
2. If I book the May 2015 trip with a Visa/public discount offer in the Fall, but in March a better Visa/public discount is offered, can I call them to switch the offers?
3. If we upgrade in May 2015 when we arrive, can only some of us in our party upgrade & not others?
4. If we upgrade in May & then book in May/June for the December trip, should we book as an AP holder since it is likely AP discounts wouldn't be posted for December yet?
5. Could/should we book as a Visa card holder instead if Visa has a better offer, but with only a room/dining package, connecting the AP for the tickets after?
6. If you book as a AP holder, do you have an option of booking a dining package or is your only option the Tables of Wonderland add-on?
7. If I upgrade in May & book the December trip either as an AP holder/no discount or a Visa holder/with % discount, but a few months before the December trip find that an AP deal is posted that is better, can I call & get that applied to my existing reservation (that might be booked with a Visa discount)?


Thanks in advance for explaining this!

 

[purple figment]

1. If I book the May 2015 trip with a Visa discount offer, can I use the gift cards to pay for it?
2. If I book the May 2015 trip with a Visa/public discount offer in the Fall, but in March a better Visa/public discount is offered, can I call them to switch the offers?
3. If we upgrade in May 2015 when we arrive, can only some of us in our party upgrade & not others?
4. If we upgrade in May & then book in May/June for the December trip, should we book as an AP holder since it is likely AP discounts wouldn't be posted for December yet?
5. Could/should we book as a Visa card holder instead if Visa has a better offer, but with only a room/dining package, connecting the AP for the tickets after?
6. If you book as a AP holder, do you have an option of booking a dining package or is your only option the Tables of Wonderland add-on?
7. If I upgrade in May & book the December trip either as an AP holder/no discount or a Visa holder/with % discount, but a few months before the December trip find that an AP deal is posted that is better, can I call & get that applied to my existing reservation (that might be booked with a Visa discount)?


Thanks in advance for explaining this!

1. I believe you have to use the Visa for the deposit, but can pay the remainder any way you want.

2. You can take advantage of a better offer by calling as long as your resort/room category are included in the offer and there are still rooms available. Because the number of rooms for a special are limited sometimes you might have to consider changing resorts or room categories.

3. Once you've checked in and received your tickets, you can upgrade individual tickets. (I'm assuming this is in reference to the one person in your group who will not be getting an AP.) Use the tickets at least once to enter a park to bring it up to that day's value before upgrading.

4 & 5. Package specials usually require tickets so if there is a Visa or public offer you would have to determine if it is worth buying the required tickets. If the special is worth it, you can save the tickets for a future trip when you don't have APs, use the tickets towards renewal of the APs or give the tickets to anyone you wish.

A room only reservation is just the room and doesn't include tickets so you would be able to link your APs to book FP+.

6. You can book a ticketless AP package with a paid dining plan. If there is a free dining special you would have to buy the required tickets to take advantage of the FD offer in spite of having APs. TiW is also a very good option and one that we've used.

7. AP specials have to be booked through the AP site or by calling. I don't know if you can modify a non-AP reservation or if you would have to book the AP special and then cancel the other res.

One note about your May 2015 and May 2016 trips. APs expire one year from the first day you use the tickets on your May 2015 trip. If you use your MYW tickets for the first time on May 10, 2014, upgrade to APs on May 12, the APs will expire on May 10, 2016 so be sure the 2016 trip ends before the APs expire.