Disclaimer: I am not a certified lactation consultant, just a breastfeeding devotee. Take my tips with a grain of salt.
1. Keep your baby in the womb (to the best of your ability) until he/she/they are considered full-term. Full-term babies are more likely to have a fully-developed suck reflex and to be better nursers from the get-go. Do whatever you can to keep your baby healthy in utero and your own stress level low. When I was pregnant with the twins, this meant swimming twice a week, taking prenatal yoga, and getting nine hours of sleep a night. It also meant going on maternity leave a few weeks early.
2. Start breastfeeding as soon as you can after birth. This is a great opportunity to draw out your baby's nursing reflex, and it will also send the message to those who are caring for you that you need support making it work. Labor and delivery nurses, midwives, and doulas are founts of information and wisdom, so pay heed!
3. Ask for help early and often. Save the money and time you would spend on attending a breastfeeding class prior to your baby's birth and spend it on lactation consultations when you return home from the hospital. With the Affordable Care Act in place, these consultations are now covered or at least partially reimbursable! Get a recommendation from a friend, your pediatrician, or OB. With the twins, I saw Cherie Tannenbaum three times and called her on at least two occasions (and it was my second time around the block!) Cherie is a wonderful resource and a twin mom to boot.
La Leche League is also a great network. It was a La Leche Leader who diagnosed me (over the phone) with thrush on the two occasions that I had it with my oldest daughter. She also told me what the treatment was so I could ensure that I got the full course of medication from my family doctor (who bless his very, very competent heart, didn't know too much about breastfeeding ailments).
4. Keep your pain in check. When I breastfed my eldest daughter, I was in excruciating pain for months. If you are in significant pain, something is likely wrong. Get help! Call upon your a lactation consultant and your doctor. This time around I managed my pain more effectively, and it made a world of difference. I used a nipple shield by day and pumped by night. Eventually I weaned my babes off of the nipple shield (they did not like the transition, but I was persistent) and switched to nursing them at night. Pumping was key both times to letting my nipples heal and managing my pain. Applying olive oil or Elicon cream (available by prescription) can help soothe angry nipples. If you have cracked or bleeding nipples, do not use a lanolin ointment like Lansinoh, as the lanolin can trap fungus and promote thrush.
5. Give it time. Both times I breastfed my kids, it took 8 weeks for it to be a breeze. That's a long time. Your mother will tell you that she doesn't remember having any problems breastfeeding. That is probably because she was a flower child and burned her bra, which in turn toughened her nipples. You will also have friends who have no trouble whatsoever with a little monster suckling their breasts. Trust that if you keep your pain under control and seek help, you can and will be successful! And if you aren't, that's ok too. I have many friends who moved their kids onto bottles and/or formula, and their babes are every bit as healthy and adorable as my own.