I just don't know anymore

Esmari I feel you.
K was much the same until she was a year old.
I breastfed her at night, and often she woke at night wanting a comfort feed. I gave it to her because it soothed her quickly and she settled back down. But she also went through a stage where she wanted to be in bed with us. She also never took a dummy nor any other comfort item, my boobs were her comfort.
She also never fell asleep on her own till she was much older, and we had to soothe her to sleep, often by use of boob or our bright stars swing which is amazing when you just dont have the patience and energy anymore.

I wish I could give you some advice. It's especially hard when only you can soothe him.
Just out of interest, does he become upset when you lie him down ie maybe he has pain? Because ear infections cause a lot of pain when they are flat on their backs. Try raising him a bit or putting him in the car seat till he's asleep and the meds have worked?
I think this had a lot to do with our problems, because K had grommets inserted just after her 1st birthday (which we spent in hospital because of her repeat infections and pneumonia) and we havent looked back since.
She now has a bed time bottle, and if she doesnt finish it I put the rest of it in her cot, and then I leave a water bottle in her cot in case she gets thirsty at night.
She really does love her milk though, so he may comfort on milk till he's older.
Dont put too much pressure on him or yourself that he grows up too quickly.
I know it's hard though, and you've really had a bad run with him.

As for sleep training, it has never worked with us unfortunately.
I think partly because every time there is a change in environment or routine it gets upset and you have to start all over again.
I think part of 'sleep training' has to do with age. They get to an age where they understand the routine that happens and that when this happens it is bed time. She is becoming less resistant to this now, but she is almost 19 months old.

Take your child for who he is, its part of his personality, and these aspects you may come to love when he's older. A doctor described Kaylee as a sensory child. She wants to be comforted, and rocked to sleep and be in your company. It's just who she is and she is most secure when in this environment.

I seem to remember both my boys went thru this, they slept like angels for a while, then all hell broke loose for a few weeks (for Brandon) / months (Liam) and then all went back to happily sleeping, then horrible sleeping etc.

A number of things could be causing it
Is he teething ?
Around this age they start to get more mobile, or start pulling themselves up or meeting some other milestone - this can cause restless sleeping
Seperation anxiety normally comes into play around 9 months, but could start earlier
Any change in routine/homelife / school can cause restless sleep

How to deal with it, that is the tough bit - sleep training (controled Crying) took 3 nights with Brandon, Liam on the other hand was tougher.
After endless research and literally trolling the internet I found my sanity saver - a book called "The No-Cry Sleep Solution" by Elizabeth Pentley, it took about 4 months but it worked. It is gentel, you stay in the room with your child, there are chapters for all sorts of situations eg weaning baby off boob / bottle / mom / being rocked to sleep etc and it is far more flexible than a lot of the methods I read - you adjust to suit YOUR home

Esmari my boy is 5 months old and I am having the exact same problem as you.
I could always put Michael in his cot and he would fall asleep on his own, DH could settle him but not anymore. I don't breastfeed but I find he drinks about 2-3 bottles at night and during the day he can stretch more. Don't know how to change that.
Michael is also on 3 meals a day (cereal in the morning, fruit for lunch and veg in the evening). He is clingy and if I try leaving him he will just scream more, to the point that he either battles to breath or he will vomit. So I refuse to leave him. Since he was born he has never taken to a dummy, it makes him gag and sometimes he will vomit too. tried various dummy brands, so I just don't bother anymore. Although it would be nice if he took it so it could soothe him.
Michael has recently started teething although nothing is about to pop as yet, so I don't know if this is the cause. But I give him calpol, prodol and sometimes ear drops too. During the day he is fine mostly, but late afternoon/early evening he will start to get difficult

Hope someone has some advice here for us

My baby will be 8 months on Tuesday. So hear is my problem:.........

He slept through the night for about 2 months, until about 2 months ago. Then suddenly he started waking again. Sometimes 3 times a night. He also used to fall asleep by himself in his cot, now suddenly he screams blue murder when it eaven looks like I am going to put him in bed. He screams so bad, that I can't calm him down without picking him up. I am breastfeeding, and am trying to 'drop' the night feeding, but he is not happy with dh calming him, he screams until I take him, then use me as a dummy. (I tried for months to get him to take a dummy, and just stopped trying) He is already on 3 meals a day, and he also feeds before every meal, and in between, and at bed time. Our routine has been the same every night. He eats, takes a bath, then the 2 of us goes to his room. Everything is calm in his room.

I have tried sleep training, but I HATE leaving him when he screams like that. And its not working. During the day it works ok, its at night that he screams like that.

Oh, and he is having 2 naps during the day now.

I just don't know anymore. I am so tired. I am also scared that maybe my milk is not good enough anymore.....

Ag, I'm just depressed. My other 2 never had this 'problems'........