With my DDs it was easy to put them in the Maya sling in the cross-cradle hold and nurse them to sleep. Sometimes I'd sway or walk with them, but they were usually fine once they got to sleep and I used this position with the Maya sling pretty easily til they were toddlers. DS, OTOH, prefers me to walk and walk and never sit still when he's in the sling, and even then, he sometimes arches his back when I try to nurse him in it. This usually happens when he chokes on milk (I have an overactive let-down reflex that really bothers him), and I have found if I position him slightly more upright, he's happier. Problem is, it's killing my back and shoulders, and he's only 2 months old! I know how to wear the Maya sling, so I know I'm not just goofing it up. I think the problem is just that I'm very petite and short-waisted. I am only 5' 1.5" (and most of that height is in my legs, not my torso) and about 115lbs and my breasts have sagged a little over the years so I have to position DS's legs and bum below my hipbone in the more upright position in order for him to lined up to latch on. This is below my center of mass and so I think it tends to strain my back muscles as they attempt to compensate for the way the weight is distributed.
Now, DS is off the charts for height (DH is very tall), so there's a lot of length of baby to try to fit, but still, he's just a couple months old and if this is hurting me already, I don't know how I'll manage as he gets bigger! I'm wondering if there's a better carrier/sling/wrap for short-waisted moms, especially for nursing while babywearing (and not necessarily in a cradle hold)...
Sarah born 04/03/02 , Ashley born 03/13/04, Rigel born 09/10/11