I had several friends who had breastfed - some easily, some not so easily, which all underlined what I'd read on MN and been told at NCT - ie, it's not necessarily the easiest thing in the world. So, I was determined to breastfeed but not rose-tinted about it - I was expecting it to be difficult.
DD was born by EMCS (though not traumatic), and was difficult to latch at first - lots of help by midwife in the recovery ward got her on for the first feed, with DH tickling her constantly to keep her awake and concentrating on feeding. We were in hospital for two days, during which we had about ten minutes of help from a (different) midwife, and although DD was feeding, it was difficult to get her to pay attention and I had to express colostrum into a syringe to be sure she'd got anything at all.
For the first 3-4 weeks feeding was painful and bad latching meant my nipples were cracked - tears aplenty, especially during night feeds. At five weeks, my nipples started to heal and now DD is six weeks old they are much better and we are doing okay.
I had thought that I'd go to breastfeeding classes, but with a CS I couldn't drive, and DH went back to work after two weeks so I was housebound several miles from where the classes are held. In addition, I was too lacking in confidence to go anyway - DH offered to take an afternoon off to drive me to a class, but I just didn't dare and preferred to struggle on at home where I felt safe. Having a friend who is a breastfeeding counsellor to chat to on facebook helped a lot, but she was the only help I've had except for a spectacularly useless health visitor ("try expressing a little to get her focussed" as milk was running down my breast, hand, arm, and dripping off my elbow...).
I will say the worst thing was the LLL "womanly art of breastfeeding" book. It has next to no pictures, is very preachy, and says "if it hurts you're doing it wrong", which made me feel completely incompetent and cry a lot. A friend lent it to me as she found it useful, but honestly I'd rather burn it. I tried laid-back breastfeeding to take the pressure off my cracked nipples, and I might as well have used red hot pokers on them, it was excruciating. That didn't make me feel any more inclined to listen to LLL!
What would have been helpful would be something that helped you once you'd already damaged your breasts/nipples. There's lots on avoiding injury, but sod all on "so you have cracked nipples, but never fear, get the latch right and it will slowly improve".
I'm hoping that as DD gets bigger we will get better at it - at six weeks it is already much easier than it was at four, and we are EBF so far so hopefully the worst has passed :)