Sleepy, but awake stopped working

I am not of the Cry It Out school of thought, but don't know what to do right now. I used to nurse Elliott to sleep and he'd go down just fine, then he pretty much started going down drowsy but awake and put himself to sleep. That's gone completely out the window and he's so sensitive to being put down now. I will admit he is crying in his crib right now because I'm really at a loss, but I'll head in there in a minute. Now that he's getting closer to a year I'm worried about creating bad habits about going to bed. He's even gotten to the point that I can't put him down unless he's nursed off of the left breast last! Needless to say, this is my new parenting dilemma and I'm sure I'll have plenty to say about it later, now I must go tend to my no nap boy!