Hey Howy, it's really exciting to see someone finally updating Weeping Town!
I have a little feedback on the terrain plan. First, that river/stream/whatever off to the east between Weeping Town and Gower looks a little off/overly simplistic to me compared with the terrain changes you're proposing. I didn't give much thought to that waterway when I added it in at the end of my project. I just needed my streams from the Rainwood to drain to the sea somehow so I cut a path for them. I wasn't really intending that waterway to be final, since I thought Weeping Town would eventually require a redo of that area anyway. So, if you did want to incorporate a redo of that waterway and the land around it into your project that would be totally fine with me.
Also, it seems like from your app you are going to leave the holdfast on the little peninsula near where that waterway drains as is. That's fine, but I just wanted to point out that holdfast is actually part of the old Weeping Town project (it's /warp weepingholdfast), not part of Gower, so it definitely could (and maybe should) be included in the redo.
One last thing, that road/trail that comes out of the Rainwood right near your Star 5 (Hamlet #3) is very important. It is the path that is described in Arianne II that Arianne and her companions take when traveling from Weeping Town to Mistwood (it passes by the cave and other points of interest mentioned in canon) So whatever path out of Weeping Town you are envisioning that Arianne took it should connect to that middle path into the Rainwood. It might be worthwhile to double check the section of Arianne II that describes the journey from Weeping Town to Mistwoood and make sure that the roads/trails you have planned connecting Weeping Town and Mistwood fit what is described.
Other than that, everything looks fantastic and I can't wait to see it.