Two from last year...
January, we paid $199 FL Res rate for a Grand Floridian garden view. Checked in and found that we got upgraded to lagoon. Our room was a corner room on the first floor of Conch Key. We had two balconies (one on the marina, and one on the lagoon) and it seemed like you could skip a rock right into the Magic Kingdom. The room was much deeper than a regular room as it was next door to a suite.
December. On December 24th, we decided to do New Years at WDW. Knowing that there were no discounts available, I called just to see if there was perhaps a rack rate room available at a value resort. None. But was offered a Caribbean Beach for $209 plus tax (yikes) and Wilderness Lodge for $395 plus tax (yikes yikes). Just as I was about to say "ok, thanks for checking for me" she muttered something under her breath that she was reading. I heard the word "upsell." She then said "How about a room at the Yacht Club for $224? You bet I took it. Holiday rack rate was $449. Then, to top it off, when I checked in we were upgraded to a water view room and we were right on Cresent Lake.