When going out and about and nursing discreetly, there is so much fabric over my LO's head (the big lower part with the tag, to make it really discreet), so even I cannot see him when nursing.

When I do not pull the lower part with tag all over and try to hide with the side pieces, it does not stay in place. The other day I went to buy fruit, my LO fell asleep while nursing and my nipple came out the wrap on my right side...I realized it probably way too late.

I find it not so easy to lower him and bring him up again when we're out. This wrap somehow does not stay in place and upper and lower him takes time to readjust the sides so he is comfy and secure.
Also when he falls asleep during nursing his head falls into "weird" positions, I have to adjust his head frequently (falls on the chest or tips back).
That is the hug hold. He does not like to be nursed in the cradle hold too much, also his head falls on his chin like that which is hard to see with all the fabric.
I am just a newbie, but really, I want something easier. I put my hopes in the headrest the MT's come with. It also makes me feel more secure if the sides cannot slide out of plce as the MT's have a solid front piece.