Not usually, but may. Inverted nipples can create a problem during breastfeeding by making it more difficult for the baby to properly latch. In some cases, they are also more prone to injury of the nipple surface. Even if the nipples don’t evert on their own, this characteristic should not prevent most women from successfully breastfeeding their children.
Probably not. Likely not. The nipples will normally protrude with adequate stimulation. Most women with inverted nipples are able to breastfeed.