Going to Disney in a big group!! Advice?

I am a seasoned Disney goer. And I have been asked to plan a group vacation with my family (2) and my GS's family (5), first time at Disney. We doing 2 rooms at POFQ (hopefully, adjoining rooms). And one of her kids will be staying in our room. Now, my question is how do you handle add-ons that depend on room assignments? For instance, my family has been to Disney so we will be a lot more laid back and have a sit down meals. We have our traditional "must go" dining restaurants. Therefore, I would like to get the DDP and since my family is small it's not that big of deal for me to spend $80 per day for meals. But, that is a different story for a family of 5 to spend $200per day on a seven day trip. And as for Disney, all members in the same room must have the same package. Therefore if I do get the dining plan at least one of her kids may have the dining plan. Should I just go with the flow and go a-la-carte for dining on this trip?
That is absolutely correct, if one of their kids is on your room reservation and you get the DDP then you all have to have the DDP, they don't make exceptions for this. Is it possible to have them get a room at POFQ that has a trundle bed as those rooms sleep 5 to avoid one of them needing to pay for the DDP and then that child can still sleep in your room. This way everyone is able to use the Magical Express, has a room card and can participate in the Extra Magic Hours? This is what I'd do so that no one gets left out of anything or has to pay more for something.
 
We have actually done this twice with 15 and 18. As stated before, impossible to stay together. However, we were able to plan to do all of the parades and major shows together. We scheduled each day at a park and discussed "the days plan" in advance. Good Luck-you will need it. Also remember this is your vacation too and you are not a paid travel guide for everyone else!
 
We went as a group of 15 in December of 2008 and are going again as a group of 18 this December. My poor sister, the Disney expert, planned the entire vacation in 2008. She planned meals and events to make each member happy. The only problem was, they weren't. Don't get me wrong, we had a fantastic time! My sister picked the perfect resort (CSR), the perfect restaurants (Booked ADRs, including character meals, WELL in advance), and the perfect days to go to the parks (touringplans.com). We had wonderful meals, no lines, pleasant weather, and gorgeous Christmas decorations. I think we went wrong in staying together all the time. Different age groups, the older family members thought we were walking too fast, the older kids moaned when they went on attractions geared toward the toddlers, the men hated the Disney bus system. At the end of the ten days, and listening to countless complaints, my sister felt like she had let our family down. She planned the entire vacation again this year, but this time she's going in with and "I'm just going to have fun" attitude. My point is that you can plan and plan and plan with each and every person in mind, but at the end of the day, you aren't going to please everyone. A group meeting is a great idea. Plan it out, then enjoy your vacation!

We booked directly through Disney's Grand Gatherings. Very simple. Once everything is booked and the deposit is made, you can make up to ten days worth of ADRs at the 180 day mark - which will help with your party size. Disney is GREAT at accomodating connecting rooms at non DVC resorts. And yes, everyone in the same room must have the EXACT same vacation plan. We are season pass holders with TIW, so it's easy for us. Sorry I can't comment on Free Dining.
 

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