Medical + Belle
Ah, well, we have no one with a specific OB/GYN specialization, however, we have two magical healers and a larger handful of renown doctors that have all dealt with pregnancies and babies. Nurse Chapel is also quite familiar, and I'm fairly sure that her and Bethany Hawke are involved in the pregnancy of another Podkru in the Mountain.
As for settlements - we're not sure yet how everyone's going to be split off. Ideally, we'll have at least two in each settlement. But at the same time, we're only going through a ten mile or so radius, nothing that's terribly far away to travel, especially with people who can fly and teleport.