Okay, so, since I have nothing else to do right now, I'm going to post our general itinerary.
As we don't yet know when we're going, I'm going to put up an itinerary for December, since that's when my mom most wants to go. If we go in October or November, the itinerary will change slightly, but probably not by much. We haven't spent Christmas with my sister since 2005, before she moved to Idaho, and have never spent Christmas with my niece. I'm also sure that not everyone will want to have my itinerary

Obviously, we won't know what exactly our itinerary will be until closer to the trip, but this is our initial plan. We don't know when the Christmas parties will be, but at some point, we're going to be going to
MVMCP and that'll be our family Christmas thing.
At some point over the course of the trip, I want our parents to be able to go to one of the signature restaurants and have a dinner for just themselves. My dad wants to go to Artist Point, and I think my mom wants to go to Narcoossee's.
I also know that the whole group of us will NOT be eating together the whole time, but these are the reservations I personally want to make, and anyone from the group who wants to join me can, and anyone who wants to go elsewhere can do that, too.
December 3-9, 2012
Monday, December 3 - Travel day. I want to keep plans as open as possible for this day. I'm not sure what our flights will look like yet. I want to fly out of Chicago early, so I'm hoping that my parents, brother, and his DGF will be willing to catch the 6am flight out of Midway. We always fly Southwest. I have absolutely no clue what Becky's family's flight will look like, since I don't know what airline they'd choose, and I also don't know if there are any direct flights from Boise to Orlando. Anyway, we'll probably have lunch at Pop and then just screw around at the resort (relax, swim, unpack, etc) until we go to dinner. I'd like for us to go to 1900 Park Fare at the Grand, since I've never been there, but have heard good things about it. Also, it's character dining, so it'd be a good way for us to make the transition from "oh god traveling are we there yet WHY AREN'T WE THERE YET" to "OMG YAY DISNEY". At least, for me.
As a surprise, I'm planning on ordering us a custom cake from the Grand Floridian bakery to be delivered during dinner. I haven't decided on a design yet, but am leaning toward something with penguins and Christmas-y things on it. I'm an amateur baker, so I love surprising people with cake or other sweet things for special (or just random) occasions.
Tuesday, December 4 - Magic Kingdom! I want this to be Jade's first park, since it's the iconic park for the Florida properties. Since my mom wants to do deluxe dining, I have us down on my spreadsheet for three meals at MK. Crystal Palace for a pre-opening breakfast, Casey's for a light lunch, and then CRT for dinner. This is the park I worked at, so I'm a walking map when it comes to getting around MK. We'll try to hit all the big rides early and then everything else later in the day. My goal for the day is to get a picture of EVERYONE in front of the castle. I also want to take Jade to BBB. My mom and sister and Josh's DGF and I might join her, but we're not sure yet.
Wednesday, December 5 - Epcot! I really think that my family will love Epcot. This plan is for December, not for if we go during F&W, which would make it change a
lot. We'd go to breakfast at Akershus, do something light at Sunshine Seasons, and then dinner at Le Cellier. I definitely want to take everyone on Spaceship Earth and make sure we all watch Illuminations.
Thursday, December 6 - DHS! Breakfast at Pop, lunch at Backlot, dinner at Sci-Fi. First things first, TOY STORY. My family's a bunch of geeks and we're all fairly competitive, so I really think they'll all love that ride. After that, definitely the Indiana Jones show and the major rides. My brother loves Indy, so I think he'd kill me if we missed it
Friday, December 7 - DAK! Breakfast at Tusker House, snacks in the middle of the day, and then a late dinner at Chef Mickey's after DAK closes. I definitely want to take my brother and sister on Everest, and I think Jade will love Kilimanjaro. My mom went on Everest and thinks my dad would love it, but he hasn't been on it yet (when I was living in Orlando, my mom came down by herself and then my dad came down a couple months later).
Saturday, December 8 - MK again! We'll likely do Kona or 'Ohana for breakfast, skip lunch, and then dinner at Liberty Tree. That would be our "Christmas dinner", so we can move it to whatever day the Christmas party is that we'll be going to. Whatever we didn't get to the first day at MK, we'll do this day.
Sunday, December 9 - Travel day

Breakfast at Pop and lunch at Captain's Grille before we leave for the airport
So, that's our tentative plan for December. We'll see how things change when we finally make a decision on when we're going.