I had a lot of problems with my first and was expecting the same again with my second and was pleasantly surprised. Angus was a good latcher and feeder and my nipples only had a slight feeling of "rawness" for a couple of days.
With Caleb I'm not sure if I was a bit slack because I had such an easy time with Angus but I ended up with a crack that turned to a bit of an ulcer which took about 3 weeks to heal. I kept persevering (toe curling pain...big ouchies) because I knew that once it was healed it would be all good - which it was and thankfully still is
I think it's good to be prepared for a few hurdles and be very wary of your attachment from the outset. If you have a few problems then take action ASAP. Nipple shields if you have to, change the way you hold bub ie football hold, or if you have to rest the nipple you can express out for one feed from that side.
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