My sons sleeping habit 😥

I seriously need to change the way my son falls asleep. He's 16 months old and half of the time he falls asleep drinking his bedtime milk, but the other half of the time he is a screaming, thrashing, tantruming nightmare. I know it is most definitely my own fault that he's so dependent on me or his dad to fall asleep but I am starting to dread his bedtime and something has to change. We've tried a few different things over the months but nothing seems to help. I wont let him cry it out (we tried once and he got so upset that he made himself throw up, never again!) and I'm just at a loss of what to do.

Just to paint a picture of what our night is like:

We always have the same routine of dinner, roughly 20ishl minutes of easy-going play time (like colouring or stacking blocks), bath, moisturising massage, short story, milk, then bed. Sometimes he is a dream and everything goes super smoothly. If it doesn't, we do the routine as normal but after his milk, he'll get restless and will want to play or will get really upset, we'll take him to our bed with the room very dimly lit, and he'll thrash/wriggle around, sometimes crying for a while or sometimes calming down quickly, until he falls asleep, and then we take him next door to his room. We never interact apart from to gently move him away from the edge of the bed or to move his hands/feet away from us.

It's not every night that it's like that, but when it is, I get so stressed and exhausted from having him on the bed with him constantly hitting/kicking/grabbing/trying to roll off of the edge/trying to initiate play, and I just can't do it anymore. I've started tracking his naps more to try and get him down when he's most tired but I'd love to be able to just put him down in his cot when he's sleepy and let him settle himself to sleep.

Is it doable? Any tips or advice welcomed!