Thanks for the suggestions everyone.
As for falling asleep:
I think part of the problem is that he is at an age where sometimes he needs a nap and sometimes he doesn't. If he takes one, he stays up forever and if he doesn't he often gets overtired.
I like the music idea. I might get something for his room.
Books used to relax him. Now they seem to give him too much to think about. He is into creating his own "fanfiction". He makes up stories about characters from different books and shows working together or against each other in new situations. I think I will try to get a set routine, start it at the same time every night and see how it goes
On waking up:
His boogeymen include the "Black Man" who he describes as a "thick shadow" that can move all over the room and the "Scary Cats" who are black with "gray rainbow eyes that swirl like oil on a sidewalk".
He also has really horrible dreams about every being dead but him. Obviously when he has a dream like this he needs to check on everyone in the family to see if we are alive. He has the hardest time after dreams like this. In general he is very concerned about the people he loves growing old and leaving him and I think these dreams are an extension of that. When he was three our 17 year old dog died and ever since then getting older has bothered him. He has always been welcomed to get in bed with us if he is scared. Threats about staying in his room have not resulted in more rest for him. We just find him sprawled out asleep in the morning with all the lights on in his room holding a toy sword. We have tried rewards and it works for a while but lately he has said he doesn't want to work on staying in bed.
He doesn't have a night light but sleeps with his door open and the bathroom light on so he isn't in complete darkness.
