A couple of observations that I posted on another thread:
Just an observation of the Dreams and Dream Squad. Most Dream Fast Passes are being handed out early in the day. This gives the guests all day to enjoy them. In fact, most of the people I spoke with who received the Fast Passes, Lanyards, and hats all told me they got there dreams early in the day, before 11:00AM. My guess is that if you want to increase your chances of winning something arrive early and go on as many attractions as you can.
Another observation is that the Dream Squad are very covert. They seem to be hiding out until its time to hand out dreams. I asked about this to a few Cast Members and they told me at the beginning of the promotion a lot of people identified the Dream Squad members and were following them around. They were even getting approached by a lot of people asking for or about the dreams. Although you will see them walking through the parks they don't roam, they tend to hide out in other places and await there time and place to hand out dreams. When we received our dream lanyards and pins at Star Tours the Dream Squad member came out of nowhere to tell us about our dream, she reached in her bag for the lanyards, handed them out and left quickly through the back exit.