I'm giving up! One of the greatest parts of baby wearing is supposed to be that you can nurse while you wear them - not so if you have small breasts and are on the short side.
DS is 19 months, and I've been trying to figure it out since he was born. It just doesn't work. My breasts are immobile - they're small, and I can't bring them up to him. I am short, so to wear him comfortably (not have him hanging down to my knees) his head ends up being right up under my chin, if not a little above. THere's like a 12+ inch differential between his head and my boobs, and I cannot figure out how to get him down there comfortably. I thought it would be easier with a SSC - nope. I loosen straps and bounce him down...down...farther down...still farther...to the point of it being really uncomfortable because his weight is down so low, and still he has to round his back and look down to latch. Not comfortable for either of us.
So unless anyone has any amazing advice, I'm throwing in the towel. Sling nursing is not going to work.