Hi there! I nursed both of my boys for at least 2 1/2 years each, through trush, plugged ducts, infected milk sinuses, mastitis, biting and a benign breast lump. I'm not telling you that you have to do the same. I'm just warning you that my advice might be a little enthusiastic about nursing, so take with a grain of salt. If you choose to continue, here's what I recommend.
1.) Lansinoh nipple ointment is made from pure lanolin and is totally safe for baby to digest. It will help with your cracked nipples in no time flat. Just apply a pea size total between both nipples after nursing and after each shower. Also, see your ped about a possible thrush infection. Check out baby's mouth, if you see the same white rash/bumps in baby's mouth, then it probably is thrush. That can also cause the cracked nipples. Thrush is a type of yeast infection very commonly passed back and forth between new mommy and nursing baby.
2.) Your breasts are going to be engorged for the first couple of months at least. More at first and gradually dropping off. I know mine were. That doesn't mean you have a clogged duct. If you get a clogged duct, you WILL know it. It starts with swelling and redness and can develop red lines on the breast around the swelling. Just remember, the more your baby nurses, the better your supply will ultimately be. Take advantage of this time of engorgement to give your breasts their marching orders for the next year or two. Nurse, nurse, nurse and if you're still engorged after nursing, then try pumping too. The more stimulation you provide, the better your supply will be.
3.) Can the lactation consultant and do what feels right for you and what makes your baby happy. I sometimes think that lactation consultants get a little too narrow minded and start thinking that things have to be done one exact way to ensure success and this is just not true. There are a million ways to breastfeed, so find what works for you and baby. Try laying down in bed with him, try the football hold, try laying on your back and letting him lay on your stomach...etc... there are about as many different ways to breastfeed as there are nursing moms. Positioning him differently just may make the difference with his latch. BTW, his latch doesn't have to be perfect, no matter what the books and LC's have to say about it. If he seems happy and it's not causing you pain (I mean after you get the nipple thing taken care of) then keep on keepin' on. As he learns to nurse better, his latch will correct itself. My sister had nipple problem just because the LC was forcing her to unlatch her daughter every minute to readjust. That's sooooo not necessary. I say, let mom and baby learn what works for them.
4.) Are you sure that you're not making that much? Is your baby gaining weight? Is he wetting 8-10 diapers a day and dirtying 3-5? Are his eyes bright and shiny, his mouth wet and his fontanel smooth (meaning, not sunken in) all of which are good signs of proper hydration? If so then you're producing plenty. It can be very difficult to get started with pumping since the stimulation is so different than a nursing baby (which is why I always recommend manual pumps so you can control the pace and rhythm to more accurately mimick your own baby). Don't count your milk supply by what you're able to express. Baby is WAY better at getting milk out of a breast than mom is, trust me.
5.) Drink tons of water and, this may sound a little odd but trust me it works, visualize. I learned this with my first and passed it on to my sister. She wouldn't believe me at first, but she finally tried it out of exasperation with me (hoping it would make me go away and quit bugging her about it :)). Take a good long drink of cool water, the get baby latched however is comfortable for you, then close your eyes and imagine that you are pushing energy from your chest out through your breasts over and over. I know it sounds corny, but this always produces let-down in every mom I've passed it on to. You've got nothing to lose by trying it anyways.
Please remember that breastfeeding isn't easy. You have to give it at least 3 solid months of trying before you can say for sure about it. It takes at least 3 months for mom and baby to get comfortable with each other and to get into a rhythm. After that, it feels like smooth sailing (until they start teething of course! lol!) It's tough, but worth it in my opinion. You'll have to make your own decision of course, but I hope my advice can help if you choose to continue.
Best wishes!