our families dogs prefer the trampoline/hammock style beds to others and prefer to be right near the door as well.
u said that he has a warm bed, would that fit in the kennel maybe?
also, our old kennel had a space heater installed in the back wall so that the kennel didnt get as cold but that was under the veranda connected to an all weather switch.
other than that i dont really have many suggestions cos our dog sleeps in her basket in our room.....