S.H.
I would try the Nuby soft tip cups that have the long tip on it first then after you get him on that for a few months move him to the regular soft nuby. I have see this work a few times. You can buy both of these at Walmart. Another thing is I would put some cereal in his last bottle before he goes to bed to see if that will help him sleep better and not wake up so much. Hope this helps!! S.