Yep, I said a trip for 20!
We're all staying at Animal Kingdom Lodge in December (82 days and counting!). I've been to Disney lots (former FL resident) but for many of our group, it's their first time, or first time in 15 years! Since so many haven't been or been recently, they have no idea the scope of things there are to do and the number of restaurants to choose from, so asking for much help from them was really unreasonable.
For our trip, we picked a few "must do" things that our large group will do together....a welcome dinner the first night, the Candlelight Processional and dinner in the middle of the week, and a farewell dinner our last night.
We'll also have some "small group" activities...all the girls, mothers,and grandmothers will do breakfast with Cinderella, the guys have a golf date, some of us are doing a backstage tour, and a date night for the parents (grandparents will babysit) and a date night for the grandparents (parents will refuse to let them have the grandkids).
For dinners, I picked a few restaruants to narrow the choices, and emailed the menus to everyone. If anyone had a favorite they were welcome to let me know, and if anyone just didn't want to do any of the restaurants, they were also to let me know (like my mom doesn't really like Mexican, so that was low on her list, but she could find something if everyone else wanted to go there). For as opinionated as our families are, everyone said they would be happy to try anything and would trust my judgement on good places to eat. On the one hand, that's a little unnerving because now I feel a little responsible for making sure everyone has a great time. But on the other hand, it's given me a little freedom to plan and I'm branching out to try lots of different restaurants, even some I've not eaten at in my more than 50 trips there! I made all our PS this past week and have only 1 PS meal per day.....the rest will be walk up, at the hotel, or last minute PS as we decide how to spend the day.
For planning...we thought it would be a good idea to do one thing together at the most each day. That way, we get the togetherness we were after, but each small family still has time to spend together without always being part of the mob. The limited number of togetherness activities also lets folks like me and my DH do what we want (parks open to close every day) while the other not-so-Disney-freaks in the family can spend time at the pool, shopping, golfing, etc. without feeling like they're skipping out on family events.
Like a few others have said above, I really enjoy the planning phase and am somewhat of a control freak, so I don't think I'd enjoy having someone else do it for me. But if it's stressing you out, then maybe turning it over to DU would be good. Just make sure you're able to enjoy the planning and the trip and aren't a total stressball when it finally arrives!!
Enjoy! And don't forget to check out the special services Disney will start offering in October for large groups travelling together. Called Magical Gatherings, the services and special events will be exclusively for groups of 8 or more. They'll have special helps with room booking, special semi-private meal events, and other services for groups. They'll be announcing all of this sometime in October....my money is on the big press event weekend October 8-10. Check with them after that to see what special things they can do for your family!
Good luck!
kadaten