Okay, jumped over here from Tim's (That's Nice) TR! I breezed through your report since there is too much to read everything, but I wanted to check out your schedule since our Disney trips are at the same time and we just might see each other roaming around the parks!
There are a couple of similarities. Gee-off and my DW (Alison) are both 6th grade math teachers!! And your Drew has a love of soccer in common with my DS13, who is also named Andrew!
So glad you guys got a Wish Trip from MAW, and will get to stay at GKTW! Looks like a super place from the early pics Tim has posted!
Couldn't help stopping at all the Big Give posts and checking out all the wonderful gifts! I never cease to be amazed at what a great job they all do, and how generous they all are!!!
Make sure they are aware of the food allergies. They are very good about having the chef speak to you about the menu, and recommending any items that you need to avoid, and recommendations that are safe!
As for your schedule, I think I found the latest update. We will be in MK that Tuesday also, but you will probably be long gone before we arrive since it will be late in the evening. After we check in at Kidani on Wednesday, we plan to also head over to Epcot. My goal is to be there no later than the time WS opens at 10:00am, which is close to the time you have your ADR at Akershus! I plan to spend a lot of time in WS trying to catch the Storytellers, so maybe our paths will cross there that morning. We have a dinner ADR at Tutto Italia later that day.
We acually plan to do MK on Thursday, and hope the crowds won't be so bad since we figure most will want to be there on NYE instead. Plus they do the NYE fireworks that night also, sort of a trial run! Most people want to do MK and Epcot on NYE, and those typically fill to capacity, but DHS also has NYE fireworks, and it usually isn't that bad then (relatively speaking). We actually did the same thing on July 4th two years ago, and the crowds there weren't bad at all and we still got to enjoy fireworks. Since we will probably be out late on NYE, we plan to do AK on the 1st since it probably won't be as crowded, and not arriving for rope drop shouldn't be a huge drawback!
One other thing I noticed and will comment on. You mentioned what to use for autographs, and the clickable Sharpie is definitely a suggestion, but I have read in places that they really don't like Sharpies for the characters to do autographs. It is too easy for them to get marks on the costumes trying to get them open with their "large" hands, unless it is someone like a princess or something that doesn't have to wear different hands than their own. Whatever you decide to get, just make sure it is larger so the costumed characters can grip it easier!!
Hope you guys have a great trip!