Hi, Stacy!
Great question!
For my family, we prefer to get the
Disney Dining Plan for several reasons. First, this prevents us from having one large bill at the end of our trip (which happens when we charge souvenirs, dining, etc., to our room). Instead, a large portion of that cost has already been paid, helping us to spread it out a bit more evenly. Next, we actually
relax more while on the Dining Plan. Because this DP includes one Table Service meal per person per night of stay, we make sure that we use that once a day, to spread out the luxury. We sit down, out of the elements, off our feet, out of the crowds for about an hour. Without the plan, we might be tempted to just grab and go most days. Finally, we all have become spoiled by ordering the best items on the menu while on the DP, because the price of the entree is irrelevant when dining on the Disney Dining Plan. (That means that I now have two young foodies in the house, too!)
For your little prince's big day, try Chef Mickey's at Disney's Contemporary Resort. The food is fantastic and you'll get to meet Mickey and Pals right at your table, no waiting in line for an autograph at the parks! It's so easy to get to, also, as you can monorail or even walk to / from Magic Kingdom.
We also love The Crystal Palace, in Magic Kingdom, for breakfast, lunch or dinner. Winnie the Pooh and Pals encourage the kids to parade, but you may find that the food will also keep you coming back in future trips.
In short, look to see where you'd like to dine and, if that includes Table Service meals, then go for the Dining Plan. If you are more of a Quick Service family, then a Quick Service Plan (paying for a character meal out of pocket) may be better for you.
Send more questions as you decide, Stacy; I'd love to help!