It sounds like you have more experience than most women, so I am not sure if there is any advice I could give that you don't already know. I do remember the feeding being very painful for the first month with my first daughter, but I have no other children (yet) to compare her nursing style to. I had to pump A LOT because I worked full time and then while she was hospitalized, she could not nurse. The pumping really didn't take too long, about 15 minutes. At work, I used two hand pumps and milked both breasts at the same time to save time. At the hospital, I was able to use the hospital-grade Medela electric pump. Oh, that was heavenly!!! It was so fast and so gentle, felt so natural compared to the hand pumps. Then I was trying to pump extra milk to freeze for use after she was weaned from me. I found it quite liberating to be able to pump a bottle and say to my husband, "Here ya go, now I'm going to the store," or, "It's your turn to get up and feed her. There's a bottle in the fridge." If you really, really, really, really want to keep feeding your little one breastmilk, don't let pumping stop you! You'll find that it fits into your routine after some adjusting.
Good luck with the LC. She'll probably have some good tips for you.
PS: Does the baby clench any less in any certain hold? I found that lying down side by side caused her to ease up more than the football hold, so I ditched the football hold completely.