Hi, Brian!
Not to worry; we have all the advice you need about making Advanced Dining Reservations for your upcoming trip to Walt Disney World...and it's your FIRST visit too! Woo hoo!
Let's get rid of the stress right now. First, decide which attractions and shows at the parks are most important to you, perhaps looking through park webpages at
Disney World.com. Let me know how many days you'll be in WDW, including the dates, days of park passes and if you'll be on a Dining Plan; I'll help you decide the best park to be in for each day of your visit. While this sounds very scheduled, and you asked for flexibility, I suggest that let your plan within each park each day be where flexibility comes in to the picture. Otherwise, you'll decide that you're feeling like dining at a particular restaurant or at a specific time that day, only to discover that that restaurant, and many other, have no available reservations. Lots of disappointment can be avoided with early planning, so let's get right on that! :-)
As such, let your ADRs be what dictates your activities for the day, planned carefully around your interests and activities in each park. For example, with a 5-year-old in tow, you might want to eat an early dinner, since bedtime might be earlier for him than other park Guests. Perhaps he's a Mickey fan; if so, dining at Chef Mickey's at Disney's Contemporary Resort would be perfect for the three of you.
While your choices do feel overwhelming, it's easy to navigate through all of them with the help of someone who's been there, done that, so send more details and we'll work together to come up with some ADRs that will turn out to be a highlight of each day on your vacation. I love to help!