I haven't done the Ceremony yet either, but hope to this trip. I think they do two per day, one to raise the flag and one to lower it in the evening. From what I've read you get to look around from the top of the Resort for a while and take pictures. Quite some view from the sound of it.
This description is taken from All Ears.Net:
The Wilderness Lodge Flag Family of the day gets to climb up to the roof of the Wilderness Lodge and assist with raising the flags for the day. (At one time you could also take the flags down, but that has stopped). It's a wonderful treat that can only be requested at check-in, prior reservations are not possible. Visit our Flag Family Scrapbook!
"We just returned from the Lodge and were the flag family. It was wonderful! We began in the lobby by meeting Darlene, our ranger, at 8:30am and actually spent a hour with her all together. She had a Lodge tour to lead at 9:30. We raised all the flags on the roof which included the Stars and Stripes, the flag of Florida, the Disney flag, and two Wilderness Lodge flags. (Jan)
During our stay at WL, we were selected to be the "flag family" one day. At 7am, they take your family up to the roof of WL so you can raise the American flag. You get to spend about 10 minutes up there, they take your picture, give you a picture frame and certificate, and treat you to breakfast afterwards. (Note not all families report being treated to breakfast!) The view is incredible! We were selected purely by accident.
I mentioned to the front desk person that I really enjoyed the tour of the WL that they give (at 9:15am). When I mentioned this to her, she asked if my family and I would like to be the "flag family" one morning. We all enjoyed the experience very much, especially my 5 yr. old daughter! I don't think many people know about this, so if you inquire early you prob. have a good chance of being selected. Thanks to Brad Feldstein for this report "
Hope that helps.