Can't help you with the weaning, but we had similar problems with DD1. Have you tried putting a radio in his room? DD1 won't sleep without it. The other thing is white noise - a heater fan, a dishwasher, or a specific white noise machine or sound machine. Both the girls have a little fan heater n their rooms at the moment as it is so cold. I turn them off when I go to bed, but I find they help so much as they are noisey in their rooms it helps keep the other noises OUT of their rooms - my doing the dishes, opening the front door, or cleaning etc. DD1 now never wakes up before I go to bed and I am sure this is why. HTH