Hang in there. I have one side that is definitely less comfortable than the other, and it seems to be getting better. I'm sure you've tried a million things, but one that helps us is that if his latch is really poor, I'll latch him in the orientation as the other. So, my left is the side he struggles with. I nurse him in cradle or cross cradle on the right, then football on the left, so that he's basically facing the same direction for both breasts. Does that make sense? It seems to help us.
DS Ethan 12/16/2008
Breast fed/pumped 11 months as a surgical resident, 80 hours a week at work
DS Abram Daniel 12/20/2012
Feel like we've gotten a strong start