This could be how it looks on the ground, before you enter it. (btw, all these maps would be bigger, this would just be what you would see on your screen) (I posted a link for the full image, too)
NPC (Marty): "The biggest windmill in the world, and now it can't even turn.. I feel bad for anyone in Fairyville or Mushroom Village that's trying to watch TV or something - without the Skymill spinning, there isn't going to be any power for a long time! They hired me to come fix it, but I can't get near it with that enormous beast up there."
(notice that reference to the kid trying to watch TV in the Mushroom Village Hotel? )
http://imageshack.us/a/img40/9508/l4vd.jpg
- Windmill1F.jpg (383.08 KiB) Viewed 2379 times
This could be what the first stage would look like, and 2 or 3 after this that look similar. Also, some monsters that are higher level than Orange Crazies but sort of look similar?
http://imageshack.us/a/img59/2966/pakv.jpg
- Windmill2F.jpg (319.2 KiB) Viewed 2379 times
This would be the final stage before the top. It wouldn't have monsters but would have tiny platforms that you'd have to jump up without falling back down.
http://imageshack.us/a/img39/3941/lobv.jpg
- Windmill3F.jpg (390.05 KiB) Viewed 2379 times
Aaaand the top floor with the broken propeller. The part you see of this floor looks the same on the other half that's not showing (it's symmetrical). The boss that I thought of (but I can't draw on the computer good enough ) is a giant, two-headed thing that has mouths like the Orange Crazy. It has tentacles, two of which reach down on both sides and block the platforms up to him. In order to get to him, you have to kill both tentacles at once (meaning you need at least two people to kill it) otherwise they just respawn instantly.
http://imageshack.us/a/img577/8923/ep4i.jpg
- Windmill4F.jpg (305.55 KiB) Viewed 2379 times
Long post, but I just wanted to see what people thought.