Does this work with parenting?

My youngest son is 2 and has not sleep through the night once in his life.

I breastfeed him at bedtime, and when he wakes up in the middle of the night, he cries and cries and won’t go back to sleep until I take him into our bed and we co-sleep + breastfeed the rest of the night. He is otherwise a very healthy, happy, delightful child.

We also have an older son who’s 5 and is sleeping well, but they share a room so there’s always the concern that son #2 crying will wake up son #1 and then we’ll have two kids to deal with in the middle of the night.

I am having conflicting thoughts/feelings about this:

– I wish he would just sleep through the night and I could have better-quality sleep.
BUT: Breastfeeding/co-sleeping are (on the whole) very sweet components of my parenting, and I know he is the last child I will have (we only want two). If I stop breastfeeding/co-sleeping now, I know I never will again.

– We should have sleep-trained him sooner, and we wouldn’t be dealing with this now.
BUT – I know it was right for us to do it this way up until now. We certainly got a lot more sleep with him in the early months than we did with his brother. (Plus: how do I know it was the right thing to do? Because we did! 😉

– Sleeping through the night is a developmental milestone and he will get to it eventually.
BUT – What if he doesn’t? What if he actually needs us to teach him how to detach + sleep through the night?

– We have tried to get him back to sleep in his own bed / night-wean him multiple times before and it has never worked. I have read all the books and nothing has helped. He can scream for (literally) hours and neither I nor my husband are comfortable letting him do that. It gets really stressful and everyone is miserable and crabby. We both have intense work lives (especially my husband) and it never seems a good time to go several nights in a row with no sleep + the stress of a child screaming.

Confusion! And I know what you think about confusion. 🙂

Have you ever coached someone through a situation like this? Is it a case of just making a decision and following through with it? Even if a screaming child is involved, and it means a string of sleepless nights with no guaranteed result?

I’m so tangled up in the emotional component I can’t see clearly. I will welcome your perspective. Thank you!