Have you looked at this baby's mouth and tongue?  Tight frenula, especially those where baby can extend the tongue, but only briefly, can lead to the "scraping" you describe.  In these cases, I often see docs just take a quick look, state that baby can extend the tongue, so no problem.  However, what seems to be happening is that the frenulum acts like a rubber band pullng the tongue back, so baby extends it again, it gets retracted again, etc. etc.
Also, when I see the "lipstick nipple" I like to exaggerate the assymetric latch.  I suggest to the mom that she position baby and breast so that it looks like she is trying to get the nipple "up the baby's nose" in order to get the lower jaw far enough on.  I have seen lots of moms start out with great approach and at the last split second, they manage to aim the nipple down just as baby "closes in".  
Of course, ideally when the baby is allowed to take the breast without interference, he/she will naturally get a "perfect" latch, but sometimes we have to be more directive.

Winnie

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