We were there from May 10=19th. Don't know how many nights people stayed in the Castle, but do know that the day we watched the parade, they introduced a family as that day's winners.
We Saw dream fastpasses around necks everyday we were there. . . at whatever park we were at. Saw enough groups of people who wore lanyards with just the 2 pins (looked like they were new . . .everyone in the group wearing them and no extra pins on them) that I think those must've been awarded every/just about every day we were there as well. Same with the Mickey ears. Last Friday, I saw first 1 dream team member, then 4 more creep up the back stairs at Tower of Terror and thought with 5 of them there, surely there was some big prize about to be awarded (everything I'd read mentioned a couple of DT members). But all I ever saw happen was a bunch of people come out of TOT with the ears. We did see a lot of dream team members (sans vests) out and about the 10 days we were there . . . answering questions, directing people, etc.
My SIL and my niece both got Tink pin sets. . . curious, does each park have a slightly different set? SIL got hers at EPCOT and they were a dark blue and niece got hers at MK and they were much lighter blue.
A DT member came up to my 5 year old and I as I was trying to read a map in front of Snow White Adventures and asked if we'd ridden it yet. I replied that DD wouldn't because she'd heard the witch was scary. The woman then spent quite a bit of time with us, giving her a packet of pixie dust that her best friend Tinkerbell gave her to pass onto a princess to scare away the witch. DD still wasn't buying. That kind woman spent close to 5 minutes talking to us, telling dd that her boss was Mickey and he wouldn't allow rides to be too scary, or for her to tell a lie about the ride, or for anyone to get hurt. Could she please pick out a "special cart" (the safest one . . .tehehe . . . for us that was Sneezy) for dd to ride in . . . dd finally caved . . .loved the ride, and the team member was waiting for us at the end of the ride to see how dd liked the ride. She gave her a certificate that proclaimed her to be the bravest princess in all of magic kingdom and thanked her for scaring the witch away. Totally made my day! And dd loved the ride. . .rode it again.
So, we didn't get ears, lanyards, or fastpasses, but dd overcame her fear of that ride due to that kind Dream Team member.
We Saw dream fastpasses around necks everyday we were there. . . at whatever park we were at. Saw enough groups of people who wore lanyards with just the 2 pins (looked like they were new . . .everyone in the group wearing them and no extra pins on them) that I think those must've been awarded every/just about every day we were there as well. Same with the Mickey ears. Last Friday, I saw first 1 dream team member, then 4 more creep up the back stairs at Tower of Terror and thought with 5 of them there, surely there was some big prize about to be awarded (everything I'd read mentioned a couple of DT members). But all I ever saw happen was a bunch of people come out of TOT with the ears. We did see a lot of dream team members (sans vests) out and about the 10 days we were there . . . answering questions, directing people, etc.
My SIL and my niece both got Tink pin sets. . . curious, does each park have a slightly different set? SIL got hers at EPCOT and they were a dark blue and niece got hers at MK and they were much lighter blue.
A DT member came up to my 5 year old and I as I was trying to read a map in front of Snow White Adventures and asked if we'd ridden it yet. I replied that DD wouldn't because she'd heard the witch was scary. The woman then spent quite a bit of time with us, giving her a packet of pixie dust that her best friend Tinkerbell gave her to pass onto a princess to scare away the witch. DD still wasn't buying. That kind woman spent close to 5 minutes talking to us, telling dd that her boss was Mickey and he wouldn't allow rides to be too scary, or for her to tell a lie about the ride, or for anyone to get hurt. Could she please pick out a "special cart" (the safest one . . .tehehe . . . for us that was Sneezy) for dd to ride in . . . dd finally caved . . .loved the ride, and the team member was waiting for us at the end of the ride to see how dd liked the ride. She gave her a certificate that proclaimed her to be the bravest princess in all of magic kingdom and thanked her for scaring the witch away. Totally made my day! And dd loved the ride. . .rode it again.
So, we didn't get ears, lanyards, or fastpasses, but dd overcame her fear of that ride due to that kind Dream Team member.
Great story and reminds of something similar that happened in 
A CM asked us to wait a second, so we did. Next thing we know, Jim the CM says he will ride with the girls while DS and I wait. That was the best thing ever! 
to things that might seem small ...to everyone but you! That's what keeps me coming back for more. 
