I’ve actually called Disney on 4 separate occasions to try and upgrade. The first was close to announcement, second was probably around 2 weeks later, third was about a week later, the fourth was last week or maybe the week before. It may of been more but I can’t remember, either way its irrelevant now.
On ALL of the times I called, I was advised to wait and upgrade at the parks. The reason why I didn't upgrade the first and second time was because of what you said you have to go 13-15 days to break even. I’m an out of state, so when I finally got a quote from them (the mind you took HOURS of been on hold) I set up a spreadsheet.
Right now I have 3 trips. 2 in incubation and 1 definite.
7 days in December
3 in late March - April (very close to definite just was waiting to upgrade pass for tickets)
An unknown amount of time in October
All with a park hopper.
I am looking at a loss now, that’s far more then it would of been because now I am going to lose the 7 day credit in December. If I would of bought the pass when it was available I could of saved hundreds of dollars. This of course all hinges on how long I stay in October if I decide to go.
Oh, and everytime I talked to a cast member they told me that all park reservations would be lost on upgrade. I had 7 for my upcoming trip in December…and really didn’t want to lose them.
I guess I could technically upgrade in April if they are still around but would have to run the numbers and see if that’s even worth it.