I have to say that I've really enjoyed reading back through the thread and seeing the map progress. I have a few points regarding some of the things here. Feel free to disregard as you see fit but hopefully something I say can be used to make this fine map even better.

The first has to do with the sample of the finished houses. The black outline for the colored texture seems abrupt. Perhaps try bringing the texture to a more natural edge while making sure that it doesn't blend into what's underneath it. The lack of chimneys was something else that stood out, although it could be that you've already planned to add those. I also noticed a lot of different colors for the roofs. I would suggest picking one and using it on most buildings (perhaps with minor shade variation) as I'm pretty sure a lot of roofing in those times was based on what kind of materials were locally available.

The new farm samples look great. I would only suggest showing those areas where the plow turned around to start a new row. The lines cut off at the edge quite abruptly.

For the trees, the samples look good in your latest farm picture. I would only suggest some size variation, shape variation, a bot more color variation and perhaps making the trees a little darker on one side. (Sun vs shade)

Anyway, I've rambled enough so I'll leave you with it.

Keep up the excellent work!