big HUGS----I can understand your feelings about him not being happy and appearing tired etc....sleep training really is a very difficult and emotional time for everyone......there was alot of crying for both my son and myself..but the I knew it was all worth it when I was finally able to do windown and leave and he fussed a bit but but fell asleep on his own..I was so shocked and happy I had to call a fellow BW (who had been helping me ) with the good news!
like I said this is all short term..
I was very worried about OT---I called my friend every day saying, he is too OT, this isnt going to work and I am being cruel...but she reminded me "what choice do you have", so I kept going. And afterwards it did [ay off because I think he got better rested after he was able to fall asleep independently.
we have only just at the age of 6months started to get longer naps and more of a rouitne. I have a spirited chap, but my older DS was exactly the same way so I had experience.
I think perhaps visit the pupd FAQ boards--there are great age appropriate pupd info.
ditch the soother==might as well since you are sleep training anyhow.