I'm a bit of a map freak and I always carry my pocket atlas with me when I fly. I fly often for work and if the weather is clear, I sometimes track the route from the west coast all the way back to Chicago (it's not good for the neck) but I can't seem to help myself.
My point in saying that is you have to have some idea of what you're looking for. WDW isn't very obvious from the sky but if you know the landmarks to look for, it helps. For example, I usually look for that World Villiage building that's kind of rusty/orange colored. It's easy to spot and right next to WDW. Then I start to look for the Swan or Dolphin or Spaceship earth. Soon enough, I'm noticing the Contemporary and Carribbean Beach Resort.
I've never noticed Cinderella's castle, Tree of Life or ToT.
I've probably flown in/out of Orlando 35 times. I've seen parts of WDW 5 times. Other than that, we either took off/landed from an area where I couldn't see it, or it was dark, or it was cloudy.
It's very difficult to get your bearings during take-off since you usually have no idea what direction you're flying. It's easier for me to see WDW upon arrival because leaving my home airport, I can immediately notice roads/buildings and know where I am in order to track the remainder of my flight.
OK, now I've shared my own private nerdiness.