In my experience support, support, support and some more support is the key when you are having a hard time trying to establish breast feeding.
DD1 - I had a terrible time. My nipples were so cracked and bleeding by day three that I had to formula feed her until they healed. Even though the hospital tried as much as they could to help me in the end I paid a lactation consultant to help. Eventually after 4-6 weeks it all fell together and I feed her until she was 14 months old.
DD2 - I thought it would be easier but it was just as hard this time. Cracked and bleeding nipples again. Having to formula feed and express while they healed again. What was invaluable to me was my hospital (different one DD1) offers a lactation clinic free of charge for the first fortnight after your baby is born. I basically went there nearly everday for help getting the attachment right. And just being able to talk to someone that was understanding and supportive helped me get through those really hard first weeks. Check to see if your hospital offers this service. Also, this time I also found changing positions constantly with DD2, ie from cradle hold to football hold, seemed to help minimise nipple damage. This time it only took about 4 weeks for everything to fall into place and it has been great ever since.
I also found using a hand or an electric pump caused more problems than solved. If you need to express at all due to damaged nipples I think it is best just to do it by hand. It is a lot slower but your nipples heal so much faster and you can't damage them any further.
I also used Lansinoh. I tried nipple shields but they did not work for me.
I wish you all the best.