I also agree that it is an individual situation based on how you eat and where during your trip.
We recently did a short 3 night trip for my ds's 8th birthday. We had CS 3 days and had 3 TS dinners during our stay. At only 1 of those dinners did I actually order something for ds#2 since he's an awful eater and frankly didn't want anything. We had 1 appie for the table, 3 entrees (2 adult and 1 child) and 1 dessert. Only at WCC did we order a second child's meal. We only ordered softdrinks at our meals.
At lunch, we ordered 2 meals and split them between the 4 of us. I ordered drinks for each of us at each CS meal. I also purchased a few boxes of popcorn, an ice pop and I think a drink.
I also purchased breakfast 1 day (2 adult meals and 1 child) and small breakfast items from the CS place at WL. I used a pre loaded debit card so I could keep track of our food spending.
I ended up spending about $385 (that is with the DDE 20% discount) for the 3 night stay. That averages out to be just over $125/day in food. Now please remember this is without ordering a dinner for my younger son 2 of the nights, no breakfast for him any day and only 2 lunches for 4 people any day.
I figure that the with the dining plan costing me $98/day and using a
AAA discount I'll do better than booking an AP rate and paying cash for meals. Yes, I have to purchase 1 day passes in order to get the dining plan. But we will be coming back again in November and if my mom comes with us, she will use the 1 day passes so they will definitely get used at some point so I'm not concerned about wasted money.
What I'm trying to say is that each family has different needs and desires out of a trip and for some, the dining plan is a great value, giving them the opportunity to plan for food costs in advance, enjoy some different, more expensive restaurants and order a bit more than they normally would. For others, they would not benefit if they stick mostly to counter service, or alternatively use TS exclusively and never use CS at all.
Hope everyone has a wonderful vacation.