This sounds very similar to my oldest ds who is now 7- he also was addicted to his bottle, needing one to fall asleep as well as several during the night, and the frequent waking up screaming. Did you have him tested for reflux? You said no GI issues but wondering if they really checked for that with an endoscopy. My ds had silent reflux- no spitting up, but terrible heartburn which gets worse when laying down and better temporarily when you wash it down with some water or milk (hence the reason why he was frequently waking up screaming and needed something to drink to go back to sleep for a little while). I put him on Prevacid and that helped. He still woke up from his naps screaming so I stopped giving him naps when he was 2 and a half and then made his bedtime 7pm. No nap also seemed to help him sleep better at night. He would sleep from 7pm-7am. I continued to cosleep with him but I had two twin beds that I pushed together so if he was fidgeting on his bed it wouldn't wake me up but if he needed me I was still right there. The bottle before bed was a comfort thing and I decided I was going to let him have that until he felt he didn't want it anymore. One night I handed him his bottle and he said, "no thank you- I don't need that anymore." And that was that- no whining or crying or struggles- he was so proud of himself that he had reached that stage where he truly didn't want it and he did that all on his own. He was 5. I know most "experts" would say that's ridiculous to let a 5 year old have a bottle but it all worked out just fine for us. I did the same thing with the cosleeping. I actually had three twin beds pushed together by then- his younger brother on one, me in the middle one, and ds on the end one. One day the boys said to me that they would like their own "kids' room" and basically kicked me out lol. I took out the middle bed, put my younger ds's bed up against one wall and my older ds' bed against the other wall, and they loved having their own space- no grown ups! They were 6 & 5 at the time- I don't regret at all letting my ds take the time he needed to feel comfortable sleeping on his own. Everyone is happy and relaxed. That whole time my husband slept in the other bedroom by himself and it did not hurt our relationship at all. We found plenty of time to spend together and honestly I think it would have been worse for us if we were always negotiating who was going to get up and soothe ds and what plan were we going to use to get him to sleep on his own this time, etc. So to make a long post even longer, my basic advise is: double check he doesn't have reflux (I would even suggest trying out the Prevacid for a couple of weeks just to see if it makes a difference, if you don't want to put him through any more tests.), get rid of the nap, and keep cosleeping and letting him have his bottle until he's ready to move on.