Hello again, Emily!
It's great to see you again. It can definitely be overwhelming planning a Walt Disney World vacation. There are so many things to see and do and options to consider! There are some vacations where the Disney Dining Plan is your best option and other times it's best to pay "out of pocket" for your meals.
If you're only planning on a couple of Character Dining Experiences for your vacation and do not plan on sitting down to a meal every day, the Disney Dining Plan may not be the best value for you. We have had vacations where we only do two or three sit down meals over a four or five night vacation, and in those cases, it works out better financially for us to pay for the meals ourselves.
Another way I make my decision is to really sit down and look at the numbers. I'll go to an unofficial site like TouringPlans.com and look at their menu and pricing information. I write down what I think we'll spend in a typical day on meals and then compare that cost to the cost of the Disney Dining Plan.
Also, keep in mind in order to qualify for the Disney Dining Plan, you must have a
Magic Your Way Vacation Package booked and everyone staying the room must have the same type of ticket and Dining Plan.
I'm running out of room, so please come back again and ask me any other questions you may have Emily. I hope I'm helping make your planning a little less overwhelming.
Pixie Dust,
Ashley