Does it hurt like this for everyone at the start or am I doing something wrong? I can't figure out what and apparently the LC couldn't either!! But how does my nipple get grazed if nothing's wrong! When she comes off it seems more sore on the top of my nipple and more pulled out. I think it should look more even but the LC said the shape was alright as long as it doesn't look flattened or have a ridge or anything.
It hurts at the start for me.

My nipples are exactly like that when DD pulls off! Doesn't sound wrong to me...

Does Grace ever pull back on the nipple, then start sucking again? Or make little kissing noises?

Sometimes Isabel does that - it means she was attached correctly but has pulled off a bit, I have to take her off and re-attach.