Wow, you are an inspiration to overplanners everywhere.

I, too, am planning a first trip to DLR this December. We'll actually be there the exact same dates as you, except flying into SNA airport instead. Am eagerly awaiting more tips and news from you, as I've not had as much time to plan as I would have liked.
I love to research and plan. My DH not so much, so it's pretty much up to me. Unfortunately, this trip planning has been super-rushed and I've not been able to research/save as much as I wanted. Originally we were going to go next spring for my son's 5th birthday. These plans have been accelerated with the news that we will be expecting another one next summer (hence the "and a Half") and I didn't want to travel in the third trimester. With the change in plans, we started looking at dates two weeks ago. Settled on one and booked hotel, a 4-day hopper, air and car just two days ago! All very rushed, but I was able to get reservations at CCI and a good car rental rate - $17 a day on Hotwire. The hotel rate was so-so, but it came so highly recommended on the boards that I went for it.
The airfare caused me some frustration. There was a sale when I first looked at dates over the weekend, but we couldn't confirm time off work until Tuesday. It went up $40 a person that day! I was bummed. However, we did manage to get a corporate discount through my DH's employer travel so it wasn't as bad as it could have been.
Your posts here are great and I will definitely be making notes of some of your tips. I, too, am shopping for Disney goodies as surprises through the trip. If you end up doing the RideMax, let me know. We are thinkign about it too and, like you, are SW engineers so the algorithms look interesting.
Here's a tip I found: If you are planning on going to
Legoland (which we are) and have a
AAA membership, you can get 10% off discount at the gate and a 2nd day pass for free. There's more information on the Legoland site too.
Have a great trip and maybe we'll see you there!