No more bottle?

DS has always been a horrible sleeper. He falls asleep with a bottle for night and naps. I know we need to get rid of bottles, but with his awful sleep habits I'm afraid and can't handle regressing to the awful sleep we were having. DH is on call for work 50% of the time and we split his time off 50/50 in the MOTN.

We have eliminated his MOTN bottles, but getting him back down can be rough - he screams the second you think of setting him in the crib. Last night we cuddled on the rocking chair, he fell asleep in y arms and the cat jumped up to lay on him and he didn't flinch, but the second we were a foot away from the crib eyes wide open and screaming. He ended up coming to sleep with me and we all had a horrible night.

I've cut it down to 3/4 milk 1/4 water. He takes a sippy of water during the day, but flips out if we try to give him a sippy at sleep time. We've done sleep training before an it worked but regressed over time. He is extremely stubborn, we tried a few weeks ago and he cried for over an hour (checks every 5, 10, 15, and then 20 mins x 2) before I gave in and let him have a bottle. I have no idea how to do this. Help?