Part 1 is a success!
I wanted him actually sleeping at 8:30 and tonight it happened. Tonight he had a big dinner, a bit of playing, a bath, a book with me, some free time in bed with his books, a back rub and then sleep. No "meaning of life" discussions tonight. I am going to look into the calming music for the nights he has trouble winding down.
My husband thinks the lack of sun light we experience in the northwest messes with his sleep so it will be interesting to see if things improve with better weather, longer days and more outside play.
Now if only we can get through the night. Him coming down the hallway to get a cuddle and go back to sleep is fine. Him coming down the hallway to get a cuddle and talk for two hours is not cool at all. Crossing my fingers!