Well, I think many of your questions have been answered and you have been given a lot to think about. But, since you are still asking here is my two cents on a couple of items;
I would not skip AK if you can help it. Plan to go in the morning for opening, and if you are lucky, EMH. The shows alone are worth the price of admission. The Festival of the Lion King, Finding Nemo, It's Tough To Be a Bug, they are all wonderful!! The rides are amazing and too be honest, you really don't have to see that many animals unless you specifically look for them!!
For a four day trip I would not get the dining plan, especially at that time of year. The reason I say this is time and the lack of it. As another poster mentioned you need to allot about 90 minutes for a sit down meal. That is a lot of time out of your short four day schedule. However, if you feel that much time for a meal is fine, then the dining plan is worth it. I am of two minds with this one. On our first trip with a four year old we had five days and did not do the dining plan. I am glad we didn't. We still had three booked (ADR's) sit dow meals that we enjoyed, but we were not under pressure to use five sit dow meals, five counter service etc.. On our second trip this past January we had eight days and we did do the dining plan. It was well worth it then because we had more time to enjoy the food and the restaurants.
You could try to see what type of ADR's you could get for the four days by calling now. If you luck out and can get some decent times at the restaurants you want then, yes do the dining plan. As your trip is only a month or so away you may find it very hard to get any ADR's in the times and places you want and it that is the case, then skip the dining plan.
Another poster said this was the Value Season, but I think it is the start of Free Dining. That promotion is huge, which means the restaurants will be really full by now with ADR's, so I would do a quick call soon to see what, if anything is still available.
Oh, one other thing on the dining plan. If you get it and find you do not use all your snack credits ( happens to many people) by the last day, then just go and pick up a bunch of pre-packaged snacks and put them in your cooler. By the end of our trip in January we had seven snack credits left on our last night. I used them all up by getting pretzels, little cookies, etc.. and just took them home!!
We have always found the resort transportation to be wonderful! Much easier than worrying about the car, paying to park, remembering where the car is, etc... The bus stops for each resort are fairly decent and with the Carribean there should be several stops as it is a large resort. YOu get to ride in an air conditioned bus and leave the car keys at home. The busses do get crowded once the park closes, so we usually hang out and shop a bit to let the crowds die down.
Oh, even with a small child we found it a pain to do an afternoon break at the resort. We had a stroller so she would nap a bit in it and we would just relax in some shade with a cool drink. With the little amount of time you have I would suggest not returning to the resort for a break, unless you really, really need it.
Oh, Pin Trading! It is a lot of fun, but it is not for everyone. If you do it I would order some pins on line first. They run about six bucks each and go up from there in the parks, so online you can get them much cheaper. My first and second time ordering them I got about 25 for $35.00 . We then bought a lanyard at the resort gift shop the first morning. The kids really loved doing the trading and I enjoyed it becasue I got to chat with a lot of CMs. It is not that time consuming in the end, but if you all do it the time might add up. Maybe just have two lanyards and share them.
Have fun. You will have an amazing trip! Please let us know, if you can, what you are calling your Trip Report.
Suz