Bridging and upgrading and discounts, oh my!

[Sunday]

ISO Disney ticket help for several ridiculously complex scenarios. You probably need to be a rocket scientist to figure this out but here goes:

I have THREE Disney vacations coming up:

1) a Disney Half Marathon trip, stay and play package, five nights, four days MYW tickets (aka The February Trip)

2) my family arrives right afterwards to join me, room only booking, eight nights, will need six days MYW tickets (aka The March Trip)

3) our annual family trip, Magical Deal package, ten nights, eight days MYW tickets (aka The August Trip)


THE PLAN:
So I need to know whether to upgrade my 4 day ticket from the February Trip to a 10 day to accommodate the March Trip, or to an annual pass to accommodate both the March AND August trip, and math is failing me.

So please help me work this through?

I have four days worth of tickets right? I need to upgrade them to ten day tickets when I arrive in February. Ten days of tickets is $400. Four days of tickets is $325. So to upgrade my ticket should cost approx. $75 right? If I keep my tickets for my beach club reservation (8 days) that means I will have to pay the $75 to upgrade my February tickets and $380 for the eight days of tickets in August = $455. But if I can change my beach club reservation to a room only, and upgrade to an annual pass ($749) instead it will cost $749 minus $325 = $424, a small savings. BUT the annual pass gets 10-20% off dining for both our March and our August trip, and if we aren't doing free dining thats a big deal right?

But it gets more complicated! To make matters weirder, there is a Canadian ticket offer right now giving 25% off and fortunately we're eligible. So to "upgrade" to a ten day ticket (on sale for $300) from a four day ticket ($325) they owe me money? So without having to pay $75, and then potentially buying the tickets now at the sale price for our August trip ($285) that means I will only have to pay $325+$285 = $610 for all the tickets I need in 2017, which is a savings of $140 over upgrading to the annual pass but I wouldn't get the annual pass dining discount, and we will definitely spend more on dining in March and August than the minimum of $1400 to break event.

Did I mention ARGH?!

Can I even upgrade my Stay and Play 4 day tickets? Can I upgrade from that 4 day ticket for free since the 10 day currently costs less than a 4 day?

What would you do?

 

[supersnoop]

Disney will bridge a ticket that purchased as part of a package, but not one that's purchased directly. Hence, you cannot "bridge" from the Canada special. Also, Disney doesn't refund on "upgrades."

Are all days of your "February" and "March" trips within 14 days? Even if those are consecutive reservations, there's 15 "days" with 13 "nights."

The long and the short of it is; the Canada ticket offer is cheaper than an AP for your two trips. ALSO, the Canada deal is only valid in advance; not in person. Therefore, you won't be able to "upgrade" to the Canada offer. Your best bet is to book three room-only reservations and buy those Canada discounted tickets now.


Now, I'll also advise you to compare the price of a room only reservation plus separate ticket versus your stay and play special. If the difference is less than $100, go with my advice above. If it's greater than $100 but less than $165, then upgrade the 4-day to a regular 10-10 ticket. If it's greater than $165, upgrade the 4-day to an AP. My bet is it will be less than $100.