Hello Sara,
Thanks for stopping by the Disney Parks Moms Panel with your question. I'm sure your magical trip is going to be full of wonderful memories with your family. One of the best ways to make those memories is meeting all the lovable characters (and a few villains, too). I have to say, I have never considered doing what you have suggested, but it definitely makes sense.
I do have a few things for you to consider as you plan those
character meals. Be sure to book meals that don't have a lot of the same characters. This way, you will be able to see more of a variety. For example, Mickey appears at Chef Mickey's, Mickey's Backyard BBQ, Tusker House, 'Ohana, and Garden Grill. Mind you, he does have different outfits. Cinderella can be found at both Cinderella's Royal Table and dinner at 1900 Park Fare. Pooh and Tigger can be found at both Crystal Palace and breakfast at 1900 Park Fare. So, just keep this in mind. Characters available at different locations can also change without notice.
You will also find that some characters are not available at dining locations and thus, the only way to meet them is through a meet and greet in the parks. A few examples are Woody and Buzz from Toy Story, Olaf from Frozen, or Tinker Bell.
I do not want to discourage you from enjoying that many character meals, but I did want to let you know that you may still have to wait in line for characters, depending on who you most want to meet. I would also suggest getting the official
My Disney Experience mobile app. You can use this free app in the parks to get the most up to date locations and meeting times of all the characters available on any given day. It is a great tool that my family uses each trip.
Have a great vacation!
~Allison L