Keep in mind that conventional wisdom tells us that free dining isn't really free. The best way to determine this is to run a mock up of all the things you would actually order and eat while on vacation and compare that cost to the total cost you would pay for a stay with "free" dining. Also keep in mind you are paying full rack rate on your room so you have to factor in which is the bigger discount, the room only discount or the dining plan discount.
Just as an example, I know I can order things ala cart on most if not all counter service meals and split things with the other members in my family. On the dining plan you get desserts that are sometimes left uneaten and you would have to pay out of pocket for appetizers (depending on the plan chosen). Another thing that drives me crazy is the buckets of soda that everyone gets on the dining plan and nobody finishes! And that mountain of fries that go in the trash UGH!
The whole comparison is really complicated with having to do the mock up but I've found that even with 3 teen boys it's too much food. The most cost effective discounts are said to be the room only discounts. You can then pay out of pocket for food costs of the actual food that you would eat and purchase park tickets from discount sellers like
Undercover Tourist.
Here are some links that will provide more reading and in depth information that hopefully will help you understand all the pro's and cons of the dining plan and free dining. I have to break the links up to get them to appear here so copy/paste them as 1 unit with no spaces to get to the sites I am trying to link to. I don't know why they won't work here on this site so this is my work around.
http: //www .disney tourist blog. com/dining-plan-2013-disney-world-costs/
http: //www .disney tourist blog .com/disney-dining-plan-v-paying-out-pocket/
These are the sites that I have used to help me understand how to get the best discounts for the trip I am planning.
I will say that years ago my parents went to WDW with my aunt and uncle. They did the deluxe dining plan and all they did was EAT! My Mom said that they were so busy running from meal to meal that they hardly had time for the parks. Now my parents really enjoyed all that eating and they didn't mind that it was the focus of their trip. That was they type of trip they wanted to do. So that is one way to do a Disney trip. My kids would rather spend their time at the parks as opposed to being shackled to a dining plan where they had to devote a chunk of time to a sit down meal every day, perhaps twice a day depending on the plan chosen. That is where we are coming from. So the bottom line is that your mileage may vary, depending upon what is important for you and the type of trip you are aiming for.
Those two links above will help you to understand what is involved and help you to decide which direction is best for your family. There is a lot of great info in those links above both pro and con for the dining plan depending on HOW you are going to use it!
Good luck!
~NM
PS. Our family's dining direction is one of the reasons why we like the Captain's Grille. You usually don't need a reservation to get in so we can go on the fly when we are ready to do the big sit down meal. Also, everyone orders what they will actually eat, whether it be the breakfast buffet or a casual dinner. It's a relaxing and quality dining experience and paying out of pocket means we only order what we are actually going to eat. I believe the Captain's Grille is the best kept secret in Disney dining!