Sleep Training......again?

I'm sitting here in my computer room, trying not to make a sound. I've turned off the volume on my computer, in case someone Skypes me. I've turned off the ringer on my cell phone. And I am praying no one calls on either of the house phones (American or Israeli #'s).
And I am listening to Sammy cry. And cry and cry and cry. Bedtime has been really rough lately. It could be because of so many reasons - I don't know which one to blame?
There is the general one - his life has been turned upside down and he is still adjusting. But I feel like he should be past that. He seems happy with his daycare, he is picking up some Hebrew here and there. And he has slept normally at times. So it's not like this Bedtime H*ll has been a constant for 4 months. It's been up and down.
There is the Ear Infection excuse. But it doesn't seem to bother him at all. We only knew he had an ear infection because he has tubes so the nasty infection leaks out. He's been on oral antibiotics and ear drops since Sunday and was on some different ear drops starting the Thursday before too.
There is the fact that I am Mommy - and he just doesn't go to sleep nicely for me. I don't know why but he always seems to go to bed earlier and nicer when Shu puts them to bed. Personally, I dread bedtime. I can't handle listening to him cry and scream. And now that he has finally decided to acknowledge us as Mommy and Daddy - his pathetic cries out for Mommmmmy and Daddddddy break my heart.
He seemed like he would go to sleep nicely. We did the whole bedtime routine, just like every night. Teeth brushing, book reading, milk drinking, and Shma, Hamalach, and Esa Enai. He lay down at first for about 1 minute. Then sat up and started crying. And that is where we are at...
The pathetic sad sounding cries have now turned into squawks "MoMMy! MoMMy!"
I'm trying to do the whole cry it out thing but come ON! I've already gone through this with him. When he was just a few months old and that's how we taught him to sleep. And he did a good job with him. We were so relieved to have a decent sleeper........after all, we had learned our lesson with Jonah. :)
And now I have to sleep train Sammy again???? Just when I am expecting another baby?? I can't imagine how Sammy will ever sleep once we have a newborn home. That's really going to throw him off.

Anyway - just thought I would post that complaint/concern out there.

Anyone with any advice? It is VERY VERY welcome!!!!
For those who don't know - Sammy and Baby will be about 21 months apart.

THANKS and wish me luck!