I travelled to WDW with my dh, ds (almost 3), DMom, and DMIL, and we stayed for a few nights over at the Swan (dh had a conference there). We then moved over to the Contemporary, where I reserved 2 garden wing rooms (requested that they be connecting so that moms could keep an eye on the boy if dh and I wanted to go out in the evening).
Anyway, we check out of the Swan and go to the CR desk to check in early on Sunday, figuring that there was no room ready, but we would leave our bags and head to the parks. MIL was going to visit a friend in the area and would be back later.
I step up, give the CM my name and information. She starts clicking the computer keys, click, click, click, then says "Oh, Mrs. S, I just wanted to let you know that we'll be upgrading you today from 2 garden wing rooms to....a 2 bedroom suite on THE CONCIERGE FLOOR." Well, you can imagine my surprise and shock at this. I start kicking dh under the counter, trying to maintain my cool the whole time, thanking her very much for this. Of course, she tells me that our rate will be the same as the cost of the 2 original rooms. We get a card with the number to call later on to see if the room is ready, and I leave a note that MIL will be arriving before us and will they please give her a room key when she arrives.
She ends up calling us later on at the parks, saying she's up on the 14th floor in a room bigger than the place dh and I were living in at the time. 2 huge bedrooms, 3 full bathrooms, living room, dining room, small kitchenette and 4 balconies. TVs, VCR, you name it. Plus all the offerings from the lounge.
I remember at the time I picked up a price sheet from the front, and the cost of the suite we were given was probably3-4 times what we were paying for our original 2 rooms. I've had wonderful times and great service since, but I've never had something like that happen ever.
So people, there is hope for the big upgrade out there. You never know when you'll have a handfull of pixie dust sprinkled on your trip.