Hi, Michelle! It does seem a little bit overwhelming! There is so much to see and do and so many choices to make, your head starts to spin after a while!
The best place to start is with your budget, as they will help you determine which resorts to look into and whether or not it is better for you to add a dining plan. You also need to figure out how many theme park days you want to do during your stay. And if that's not enough to think about, if you are planning to do any table service restaurants - especially character dining experiences, you'll want to book them as early as possible. You can begin booking advanced dining reservations at 180 days before your arrival.
There is some excellent planning information at
www.disneyworld.com . You can even find tips here on traveling with little ones! I recommend planning to spend a bit of time there, just looking at all of your choices, then you can start narrowing things down.
Something to keep in mind - what are your priorities? Would you rather spend a day or two less in the theme parks in exchange for an upgraded accommodation? If budget is not a big concern, would you rather be at a resort on the monorail, which gives you easier access to the Magic Kingdom and EPCOT; or would you rather have a unique resort experience, like a savannah view room at Animal Kingdom Lodge? Including a dining plan helps you plan in advance for more of your budget, but if you plan on eating outside of Walt Disney World, it may not be to your benefit.
We are here to help you the whole way through to your magical vacation! Feel free to come back with any and all questions!