9:48 PM
....heheheh. Okay, so instead of debris creating difficult terrain, make it ice.
The dragon's been freezing the town as he rips it apart.
The dragon's icewalk will let it ignore the effects of the ice.
Also, add this ice effect: when a creature is pushed, pulled, or slid more than 1 square, it also falls prone at the end of the forced movement.
I will also point out that the dragon can fly, and for the first part of the session it should probably be using Dark Assault by flying down to the ground, moving through enemies' squares, then going airborne again at the end.
When it's bloodied, and has a massive boost to its chance to do critical hits, then it should get into melee, lashing out with claw and dragon's fury to make as many attacks as possible.
Before it's bloodied, play it canny and ranged.