Sleep training and vomiting

[BrownEyedSquirrel]

DS is 19 months and has always been a shite sleeper. He takes forever to get to sleep and wakes every 2-3 hours. Asleep by 8pm and awake at 6.30am.
I had assumed a lot of this was due to BF but I recently night weaned and he is still waking all the time.
I've tried gentle sleep training but it keeps failing because DS can't cry without vomiting. Unless I'm cuddling or BFing him, he cries.
After about 4 or 5 minutes of crying he'll inevitably gag and bring up his whole dinner. He's then (understandably) upset and more awake than ever.
At 6 months / 9 months / 12 months etc. I had to stop sleep training after a few days because of the vomiting but I just can't take it anymore. I'm so damn tired. I thought his sleep would be better at this age but it's shocking.
Anyone who experienced similar that can help?

You could make sure he has his dinner plenty of time before bedtime. Also don't give bedtime milk. If his tummy is emptier come bedtime he's less likely to be sick. Plus not having to digest food overnight may well improve his sleep.

Does he have a comfort mechanism now he's not feeding to sleep?

That's helpful, thank you.
He does have a BF close to sleep time so I'm going to try doing this earlier.
We've introduced a little Teddy as a comforter which he's taken to well, yes.

Does he sleep better if you co-sleep ?

@dinosaurdiana yes, for sure. We end up co sleeping from 1am as it's easier for everyone.

My LO used to do this and she did grow out of the vomiting when she cries - she's virtually 2 now (still a shit sleeper but without the vom)!

same thing with DS1 when he was 8m old.
I tried it for 2 consecutive nights, against my better judgement - half an hour screaming then puking both nights.

so on the second night I apologised to him and promised him that I'd never do it again to him or any future siblings. and I didn't.
I resigned to him staying up until 11-12pm.

around 14-15 months he started needing to sleep earlier, eventually he had an 8-9pm bedtime.
he's almost 20 and still an owl, like me.

I never even tried with my other kids.

He's still young. It's normal for him to be waking.