My son was always on the go too, he liked to go anywhere and would get stir crazy when we were home, who am I kidding he still does. I dont think there is anything wrong with it, he is just a go getter and wants to conquer the world. As far as the milk goes is he just with a sippy or a bottle? I let my son go to bed with milk until he was about 3 i know they say it is horrible for them but his teeth are perfect from what the dentist said, he was on a sippy though since the bottles allow the milk to continuously drip and puddle in their mouths. Just brush his teeth morning and night to help with the "sugar bugs" He is finally on water but he still needs his cup to go to bed. I think its just cuddling with it but once we got him to water he wouldnt ask for more milk in the middle of the night and throw a fit when he wouldnt get it.