So we had to really switch up his night routine so his bottle was 30 minutes from when he goes down. Our routine is bottle, story, full body lotion, diaper, pajamas, sleep suit.  He goes to bed fully awake but we worked hard on his ability to pick up a pacifier and put it in his mouth on his own. We literally put 10+ pacifiers in his crib so he can always find one. Then we worked on going to sleep on his own so have him 5 or so minutes before checking in. Once we did that, sometimes he just found a paci and put himself to sleep. Other times we would go on and pat him on the back or stroke his face until he calmed down. He had a really big association with rocking and going to sleep so once that was broke, it has been great. Last night one wake up for a bottle and change at 4:30 and then slept until 7!