Definitely try to be the flag family! You must request this at check-in, first thing, as there are a limited number of slots. Essentially, your family goes with a CM to the roof of the WL to raise the various flags that fly above the Lodge.
We had the opportunity to do this on our last trip and it was great! Of course, my DF had a bit of trouble with his flag so for the entire day we could look up at the top of the Lodge, see a tangled up flag, and totally abuse DF forever. Anyway, you have a beautiful view of the contemporary, magic kingdom, Bay Lake, etc. On a clear day you cann see all four icons from the parks.
It really is a wonderful experience.