Do you get your own agent assigned to you? Don't they make your dining arrangements for you? If you're booking online, how do you let them know it's a grand gathering, do you have to go link all your rooms together later?
When we made our intial reservation, one person become the "gathering leader" and made intial reservations for the group. The group then had about a week to make their deposits to their individual resort reservations.
Everyone in the group is given the same Grand Gathering ID Number, and then separate resort or package reservation numbers.
Also, instead of calling the regular Disney line, you are given a Disney Grand Gathering telephone number that is separate from the regular reservations line, and you can book the Grand Gathering exclusive dining and excursions through there, as well as making any modifications/payments to your resort reservation.
You make your regular dining arrangements through the regular dining phone line, but also give them your Grand Gathering ID Number. Same with regular tours, you use the regular tour phone line.
We picked our resort based on everyone's budget. We had originally booked into a Value, but after some discussion and consideration, upgraded to moderate, as we found out that one party in our GG would not stay on Disney property (they are timeshare holders and wanted to use their points to stay off property rather than paying out for accomodations). It didn't matter, as we still had enough of us staying on property to qualify for our Grand Gathering. We based our moderate resort on proximity, recreation, and theming. A few of us had stayed at some of the other moderates, too, so personal preference came into play. We also researched through the WDW guides and internet sites and came up with PO Riverside, (which is the highest rated/reviewed moderate on property by both AllEars and Birnbaum's).
Hope this helps.