Doc E's kennel looks great. I really like the tree in there. Another suggestion would be to build the kennel with one solid wall...the dog might feel more secure, not having to turn circles all the time to know what's around him. Might make him feel like nothing can sneak up on him. Also, consider putting this wall in such a way as to block winter winds from the dog, but allow summer breeze to hit the dog. My kennel has a three walled, roofed stable setup at the end of it that will block cold north winds, but faces open to the south so that the cool breeze comes right on in over the dog. He likes it, I think
Might also give him a wooden bench or anything he can jump up onto (not close to the fence unless the kennel has a full roof). 55 gallon barrels make good houses, only don't put a door on it up there becuase if you do, the dog's breath can create a cold condensation on the inside. Straw is good for the winter in the house, and nothing is needed for the summer, usually. Cedar shavings are supposed to be warm, too, and they also have those outdoor/waterproof pillow looking dog beds that can go in a house. Here is a pic of my pup's house...he's about 4 months in this picture, he's gettin' quite a bit bigger now.