A little late to the party here, but I hope I can offer some constructive input. I've gone the first week of December (2012) and the week right after Thanksgiving (2011) and the trip last year was even made with a 7 month old... And while I don't typically share my kids' names on the Dis, let me just say we've got a whole lot of things in common here.
There is a lot going on that week in Disney, and a part of me doesn’t want to be anywhere near the chaos while its underway.
Don't worry about it. It is a great week to be there! The parade isn't too big of a deal. Just don't go to MK that Saturday morning. We actually went on a Friday morning when they were filming concerts and had Fantasyland to ourselves with a nice soundtrack. The park did get crowded around noon, so we left MK and went to EPCOT. I just don't think having to work around a couple of mornings in MK is too big a deal with the typically lower crowds that week.
Pop Warner isn't a big deal as long as you don't stay at one of their resorts.
We’re just not moderate people.
I can't disagree. I feel exactly the same way.
I read someone TR who stayed at Coronado with the Pop Warner kids, and they said their little one woke up once because of the teenagers.
I think I've heard that story...
The more time that passes, the more I’m looking forward to giving Pop another chance.
I'd think that POP would definitely have a hard time living up to any kind of expectation after a cruise. I mean they always say that if you're doing a split stay, make sure the deluxe comes after the value. I really do like POP, a lot, so hopefully you'll enjoy it. If you end up staying there...
I’ve accepted the price I’m paying for Pop, and if that’s what I’m stuck with, so be it. I just really hope that’s not the case.
Well, I hate to throw another question mark into your resort plans, but they typically reserve blocks in resorts for POP Warner that would block out the discounts for those resorts, yet they don't announce which exact resorts they use for Pop Warner until a few months out... (that's how we got burned at CSR after we'd already booked there). I would be concerned that if All Star Sports is the only Moderate or Value with any discounted rooms available, that maybe they're not planning to put Pop Warner there since there's no food court. Purely speculation on my part, but I'd be a little concerned about it.
Did you happen to ask about availability at those resorts if you were to check out
before the 6th?
How do folks get anything accomplished with a baby?!?!
At that age, easily!!! It's when they get a little older and more independent that it gets more difficult!

This morning the CM on the phone said Saratoga Springs and Old Key West had a military room available, but I know those are primarily DVC rooms, and I’m so unfamiliar with them that I have no idea what the resort themselves are actually like.
Are they worth considering?
Well, I don't know the dollars and cents of it, but I'd definitely look into it! I've never stayed at OKW, but I know I've heard it said that those rooms are about the biggest you can get.
-Read up on baby care centers and stroller parking areas
We never used the Baby Care centers much. It is a nice quite A/C place if you need a break in the park, but we were mostly doing diaper changes in the park and it typically just made more sense to head to the nearest restroom. DD was on formula by the time we went though, so this might not be relevant to you.
-Decide ahead of time which attractions to avoid due to Landon being scared/uncomfortable
I wouldn't think you'll have any problems here. Maybe just be ready to cover his ears when there are loud noises? DD seemed to enjoy everything when she was that age. She just took it all in and was really too young to be scared if that makes sense. DS, on the other hand, taking trips at almost 2 and then almost 3 was aware enough of his surroundings that he had certain things he just didn't like.
-Figure out what/how much baby stuff to pack and what I can have my mom bring down for us
Just a tip for the parks. We packed a bag with the essentials that we carried everywhere with us and put some extra snacks, clothes, blankets, etc that we weren't too concerned about possibly losing in a bag that we just left under the stroller. I wouldn't leave anything of value like that, but nothing ever disappeared.
I suppose it’s the unknown that’s freaking me out right now. I could tour Disney blindfolded if it was just us adults going, but adding a baby to the mix has my head all kinds of confused. The main focus for me is creating a magical first trip for Landon without overwhelming and exhausting him.
Just have a general game plan in place, but be ready to change plans at any time. I'm sure he'll be fine. And most importantly, if he falls asleep in the stroller, take advantage of that time to use rider swap and do some of the things he can't ride!
