I may not do much greater shading, but there will be additional shadows that aren't in this image. Shadows are going to be done is a separate layer by applying 30% translucent solid black shapes. There's some shadowing built into the tileset (like the rooftop ledge) but for the most part, it'll be done separately. I have not tried this technique yet, so I don't know how well it will work. I'm hoping it will be something that will save considerably on time and extra tiles.
I agree that the roads look odd. If you'd care to elaborate, maybe that would help me figure out why they look odd.
Texture, contrast, and heavy shading are a stylistic choice I'm avoiding. I want to minimize such things as much as possible to get a more cartoony, Earthbound feel.
This is a daytime scene. For nighttime scenes, I'll apply a 20% navy blue overlay over the top of it. This project would feature the town at various levels of zombie infestation, so while there will be tiles for boarded up windows and barricades, I'm starting with the town before a zombie attack so that these other additional features may be built on top of it. I'm hoping for a one to one replacement deal, so that I can replace an open window with a boarded up window, or door with a barricaded door and so on. But that's for later. Nighttime will be accomplished with a 20% navy blue layer applied on top.