I personally am not a cry it out fan. I wouldn't use that technique of settling on any baby regardless of age. I'm not knocking you or anyone else who does use it.

I think wrapping him & some soothing settling techniques like patting, rocking, singing, music etc is a nicer way. I have always fed my kids to sleep. Are you BFing? Maybe you would like to try feeding him to sleep if you are bfing. Another thing I found that worked with my oldest was to lie with him in our big bed. Once he was asleep I would move him to his cot. I made it easier to move him by having him on a blanket that I could pick up like a hammock to move him. It was a good way of moving with little movement so he never woke. I would also lie him either on top of or put with him one of my t-shirts I had been wearing so he could still smell me close by.
Picking up on his tired signs is also a big thing. I made the mistake with my oldest thinking he was getting bord when he would start to get grizzly. So I tried to amuse him. It wasn't till I watched a video that the early childhood nurse brought round about settling etc (was actually this video that showed me that CIO wasn't for me) that I realised what I was missing. have a look at the main BB site , there is bound to be an artical on the tired signs.

Hope things settle down for you soon.