Let me just say that I think this is the longest post I have ever written in the history of this website. I'm not going to go into any SPECIAL planning details here, or money saving tips or anything like that. This is just the information that was specific to OUR trip; I don't have anything here about touring the parks or which rides are best for what ages or what restaurants we recommend (HA HA HA LIKE WE ATE IN A RESTAURANT). This is pretty much preparation-based only. But if you have other questions, PLEASE don't hesitate to ask.
We'll start with the basic details of our trip, so that you know exactly what we did. Sometimes that helps people who are starting with nothing and have no idea where to begin.
Our party consisted of me, Dave, Asher (age 5 at time of travel) and Lucy (age 2 at time of travel). Complicating things a bit was the fact that we also traveled with my brother, my sister-in-law, my niece (age 4 at time of travel) and nephew (age 17 months at time of travel), as well as my mom and dad, a total party of 10. We stayed for four nights at the Wilderness Lodge, and we had five-day theme park tickets and a quick-service dining plan.
Booking would have been pretty tricky if we hadn't used a travel agency. Booking three separate parties at the same time is not my idea of a fun experience, so we booked our entire vacation (sans flights) with Small World Vacations. This agency is recommended by the Unofficial Guide to Walt Disney World, the BEST travel book on the subject of Disney (the authors' website, touringplans.com, is also an amazing resource for planning). Small World Vacations is an authorized Disney vacation planner – there are no booking fees or hidden costs – meaning that the money they make is from kickbacks from Disney, not from customers. When you book through Small World, you're really booking direct with Disney. All I had to do was send an email that listed the information about our party, and within a couple of hours, I had an email from an agent who TOTALLY UNDERSTOOD everything I was asking for and made it sound perfectly simple to coordinate. The email contained a price estimate.
Although we had our estimate in hand, we didn't book until we found a really great discount code (I signed up for Disney emails at the Disney website, I believe) that gave us 40 percent off our room rate. Here's where the travel agent part really came in handy. I asked if we should hold out for a free dining package, and she told me that the value of the hotel discount would be more than a free dining package was worth. I would never have known that on my own. She was also able to tell me that the coupon code was good for booking three rooms total, which meant I could go ahead and book my brother's room and my parents' room with the discount code only I had received. Again: maybe not something I would have been able to swing doing it all by myself. HIGHLY RECOMMEND taking this route if you've never booked with Disney before. Plus: it was handled all by email. I never spoke to anyone by phone, and whenever I had a question or wanted to change something on our reservation, I sent off a quick email and heard back by the end of the day.
The other thing about travel agents is that they can be on the lookout for discounts that can be applied to already existing reservations. Meaning that if we'd booked and THEN found a coupon or a discount, our reservation could have been easily adjusted by our travel agent. That wasn't something I wanted to do on my own.
Another good decision we made was traveling in the beginning of December. Air travel is typically pretty light before the holidays hit, so we scored round trip tickets on JetBlue for $178/pp (that price includes taxes). The airports weren't super crowded and travel was easy. It also meant that the crowds were relatively light in the parks. We spent 2.5 days in the Magic Kingdom and it almost got BORING because we were able to ride whatever we wanted, WHENEVER we wanted, without standing in line for more than 10 minutes, EVER. We walked right on to most rides, including the big ones like Space Mountain, Big Thunder Mountain (Asher's favorite) and Splash Mountain (Asher's LEAST favorite, he will never forgive us for getting water in his face). (I will mention here that those are the only three rides in the Magic Kingdom park that have height restrictions; everything else is ridable by EVERYONE.) Plus the parks and our hotel were decked out in gorgeous holiday decorations. That part was super fun and festive. We did have some rain (December is one of Florida's rainiest months) but at least it was WARM rain, not cold rain. Highs were in the mid-70s and lows were in the upper 50s for our entire stay. That translates to shorts and t-shirts during the day, layered with some long-sleeves or sweatshirts in the evenings/early mornings. Jeans made me a TAD BIT too sweaty during the day.
The OTHER reason we went in December was so we could get away with not having to pay for Lucy. Kids don't need park tickets for entry until they're three, so Lucy was at the perfect age to enjoy everything, but WE DIDN'T HAVE TO PAY FOR HER TO DO SO. She also didn't qualify for the dining plan as a two-year-old, so we paid for three people to eat, and there was MORE than enough food for her to just eat off of our plates. Actually, Asher was the one who ate off of people's plates; more often than not, it was Lucy who ate the kid's meal (Asher remains our VERY picky eater).
We purchased the quick service dining plan – this meant that for every night we stayed in our hotel, we got two meals and two snacks per person (except for Lucy). It was more than enough food – each meal included an entree, a side, a drink AND A DESSERT. There was so much chocolate cake eating, you guys. SO MUCH. AT EVERY MEAL. The snack credits could be used for ice cream or drinks, but we mostly used them to buy bagels and muffins for breakfast at our hotel. The dining plan probably didn't end up saving us that much money, if any – what it DID was make eating in the parks super easy. We spent VERY little cash on food (FINE, if you MUST KNOW, I needed CORN DOGS on our last day), which meant that whatever money we had in our pockets was used for souvenirs or other things. It was really nice not having to worry about cash – our room keys were used to “pay” for our meals, and when you're trying to corral two kids in a mob of people in a very tiny restaurant, it was so nice not to have to worry about dealing out (or dropping) cash. It also helped us budget – we paid upfront, so we knew exactly how much we spent on food. With four small kids among us, we did NOT want to do any sit-down restaurants, so every meal we ate was at a counter service restaurant, where you order your food and take it back to your table with you. This was fine for five days, but I don't know if I could have done it for much longer. That's the one con of the quick-service plan – you CAN find food that isn't hamburgers or pizza, but it isn't always CONVENIENT. So, we ate a lot of hamburgers and pizza. I think we DID pay for two meals out of pocket on the day we departed (breakfast and lunch).
We stayed at the Wilderness Lodge for two major reasons. One, it is considered a Deluxe category resort (but has the lowest prices of any Deluxe hotel), and two, it has boat transportation to the Magic Kingdom. Disney makes it relatively easy to get to any part of the property via its bus system – the problem with the bus system is that it takes a decent amount of time and if you have a stroller, YOU MUST FOLD IT UP WHEN YOU GET ON THE BUS. This is difficult when you have a double stroller, two children to wrangle, and stuff stored in the baskets of the stroller. It was... well, it was MESSY every time we had to do it, let's just say that. And the monorail resorts are great, but expensive, and when the park closes at night, they can be PACKED LIKE SARDINES. The boat to the Magic Kingdom (where we spent the bulk of our time) was SO EASY: it pulled up to the dock in front of our hotel, we wheeled the double stroller onto the boat (NEVER HAD TO FOLD IT UP), and we were at the front gates of the park in five-ish or so minutes. This was particularly great on the day we went back to our hotel for a nap – the trip was quick and painless. We never EVER had to wait for a second boat because a first boat was too full to take us. It was a very good decision. (Plus the hotel itself is really beautiful.)

Other smart decisions:
Buying a double stroller on Craigslist
Asher is too old to ride in a stroller when it comes to EVERYDAY USE, but we purchased a used Maclaren Twin Techno for $75 just for this specific trip. It folded up small, fit through doorways, allowed our children to sit side by side (HUGE for them, they want to be able to see and talk to each other at all times), had plenty of storage underneath, and could hold 55 pounds of child per side. Asher walked a lot more than I expected him to, but having the stroller was essential for Lucy, and it proved to be a bonus to have all the storage available underneath. We opted to buy a used one off Craigslist so that we could resell it when we were finished with it. You CAN rent strollers at Disney – but the ones available inside the parks are the hard shell strollers without cushioning, and you can't take them OUT of the park. That's frustrating when you have a tired kid and you still need to walk them out of the gates, down to the boat dock or to the bus stop, and then through an enormous hotel. You can also rent strollers through some local companies who will deliver a really nice Baby Jogger City Mini to your hotel, but the cost was actually going to be more than buying a used one and bringing it with us. Plus, we wanted to have it available to us in the airport. The only possible solution that would have worked equally well for us was having two umbrella strollers instead of one double, in case we'd wanted to split up. There were a few times we DID split up, but during those times Asher didn't use the stroller at all, so it wouldn't have made sense to be lugging TWO of them around.

(Is that the ugliest stuffed animal you've EVER SEEN? It's a Baby Bambi. It gets wrapped in a blanket, but Lucy HATED the blanket, so now it's shriveled little legs are exposed and it is SO UGLY, YOU GUYS.)
Sending a box of snacks ahead to the hotel
Knowing we would have picky eaters with us spurred me to do this. Asher is a really annoying kind of picky, like he won't eat a FRENCH FRY unless its the RIGHT KIND OF FRENCH FRY, and I didn't want to ruin my entire vacation trying to force him to eat food we'd already paid for. So we gave most of his meals to Lucy, let him eat soft pretzels and the snacks I'd sent ahead. The hotel held the box until we arrived and we had it sent to our room after we checked in. It meant that I didn't have extra weight in our bags, nor did I run the risk of the snacks all getting crushed by airport baggage. I sent basic stuff like small bags of pretzels, goldfish, peanut butter crackers, Pirate's Booty, lollipops, M&Ms, and granola bars. Let me just tell you: LIFESAVER. Having snacks with us was great when we were in between meals or standing in a line (not that we did much of this but it did help when we stood in line for Toy Story Mania for 90 minutes), and it was nice to have in a pinch when we got back to the hotel room at night and the kids (or, uh, I) needed a pre-bedtime snack.
NOT having a day of rest
Now, if we were staying for a week or more, it would have made total sense to slow down the pace. But we arrived after noon on a Sunday, and had to leave again at noon on a Thursday, so we had to pack EVERYTHING into four full days. So we just didn't stop. We arrived, checked in to the hotel, and hit up the park. On Monday, we did go back to our hotel around 2pm to take a nap (Lucy), but we were back at it by 5pm and stayed out until well past 10:30. We really pushed the kids to their max, but they were doing great. If they'd been complaining or whiny, we definitely would have scaled back, but knowing we were only there for a short time meant we didn't have time to poke around. It helped that the parks weren't crowded, so we were able to do 98 percent of everything we wanted to do (we skipped Epcot altogether this round). I wouldn't do it any other way with little kids. The worst part of the trip for me was just staying in that tiny hotel room with them – if we'd stayed for 7 nights, I would have gone insane in there. So even though everyone says take your time! Stop for naps! Schedule a swim day!... we just didn't. And it worked for us. Four days at max pace was perfection. Also, any longer and I think they would have been downright SPOILED. I mean, we came home with FOUR ADDITIONAL STUFFED ANIMALS, you guys. FOUR!
Ok, was that long enough? (You: YES, OMG MAKE IT STOP.) If you have questions, leave a comment, and I'll leave an answer there so we have a record of it. That is, if you even MADE IT THROUGH this whole thing.