[Luvsun]

As others have said, I believe that the dreams given are random. We received our dream just by walking from Toontown to Fantasyland - just 3 ladies walking and talking about being the MK and what our plan was for the day as it was early - around 9:30 I think. The Dream Squad approached us and just started chatting with us. They asked us how our vacation was going, where we were from, who all was with us. When they found out that it was an all girls trip, they told us they thought they had something we all would thoroughly love! They asked us to wait, as one of the dream squad needed to make a phone call! A few minutes later they asked us if our entire party could be back up front at the MK to meet someone special. Of course we can - was our reply! They were all very sweet and very upbeat! Our dream was a one on one meet with Cinderella! We got to talk with her, have pictures with her. It was a great time!
This last visit, while walking past the Crystal Palace, my niece and I were talking about the schedule for meeting Peter Pan (my niece's favorite character) when walking right beside Carly was a member of the dream team. She overheard our conversation and started chatting with us. Once we got to Adventureland, she asked us to stop - she needed to make a phone call! When she came back she told us where to stand to meet Peter. She told us not to leave the area. Well, of course we didn't!
The CM came back just about the time Peter Pan and Wendy came out for meet and greets. Carly got to meet her favorite charcter and have a long chat with him. Then the CM gave Carly an official certificate that makes her an "honorary lost girl"! She also had to say a pledge about never growing up! It was so cute!
So - after that long story......yes, I think the Dream Team just cues in to people as they are already having a magical time!