Thanks for reading (and responding) to my private message.
Two final points that you may want to consider:
1) H1 KotS is rather explicit in that "small thatched homes stand around Winterhaven" (outside of the walls).
2) H1 KotS indicates that Winterhaven has a population of 977, which most likely includes those living outside the walls in those small thatched homes. (For sake of comparison, Fallcrest has a population of 1,350 with an additional 900 living within a few miles of the town.)
As before, I look forward to your next "doodle" of Winterhaven.