Re: Going to try one more time and need advice
First and foremost, try not to think of your bad experiences nursing, and know that each babe is different! Go into it relaxed, and things will come much more easily - you'll even feel more confident getting through the nursing humps that many women encounter.
Secondly, definitely get in touch with LLL or a private lactation consultant. Especially if this babe is preterm, as well. Premies can have a more difficult time latching and sucking well. Also, it's possible to nurse after pumping for a couple of weeks, but there's nothing like a baby's suck to bring milk in/increase supply. A consultant or LLL leader would be able to give you pumping advice if you need to go that route again this time.
Lastly (and another reason why a consultant would really help) - seriously cracked/sore nipples are almost always due to a latch problem. The slightest change in angle or hold can make a world of difference.
Here are some remedies for nipples that are sore/cracked (beyond the routine newborn tugging discomfort): pure lanolin ointment, olive oil, expressed breast milk (allow to air dry). Also, for cracked nipples, soaking the nipple in a medicine cup-full of normal saline (purchase at drugstore or make your own) at each feeding time really really helps heal the skin. No perfumed lotions or soaps should ever be used on nipples (they're irritants).
Feeding should be a happy time for you and the baby! Good luck and stay positive!!!