My daughter also had a very hard time latching, but I was told it was because I had 'unusually' large nipples. I SUFFERED through the pain for over 3 months even after seeing a lactation consultant. It didn't quite help, even though it really seemed like she knew what she was doing. I was seriously thinking about giving up on the bf'ing because it was sooo painful! Someone on this site suggested taking my baby to a craniosarcal therapist or a chiropractior. The reason I pursued that is becuased a googled a bunch of stuff on 'tramatic' births and a baby's subsequent need for 'realignment'. I love my chiropractor who also sees infants. My baby was a suction birth and my first one came out with just me pushing (and an epidural). My first one had no issues latching and she was born a touch smaller than my 2nd. After our 2nd visit with the chiropractor, my 2nd baby latched on just fine! No more pain. The types of adjustments done are not at all the type they do on adults...it was basically massaging their neck and spine and using the activator or clicker...very tame stuff. My baby also seemed to favor her right side and her head was starting get flatter on one side because she'd prefer to lay a certain way. That was the other reason why I was convinced that this was something beyond a lactation consultation. My chiropractor is Dr Scott Hammons with Essential Chiropractor. He's located in Bellevue, but was worth the drive for me!
http://www.babiestoday.com/articles/guiding-babys-develop...
Good luck! I am forever convinced that Dr Scott did the trick!