OH MAN now I’m trying to remember what it is they say is weird about how Sharon does maps and takes records — I really really like your ‘steerswoman off a check-in ship’ hypothesis.
I’ll keep you posted as I’m probably going to go back and reread the whole series. I didn’t quite get it right about the wizards—the new thing is the expansion of the wizards’ holdings outside The Crags for the first time, to Wulfshaven, and Sharon obliquely refers to it and seems to approve, but later in life regrets it bitterly. That’s the status quo for two hundred years and then wizards move into Donner—sending dragons first, so that the population will be grateful to them—and one other, unnamed place.
It sounds to me like the two first wizards’ holdings are the landing points for the ships, and that Sharon must have also been one of the first landing party if my hypothesis is true, a scout or something.