Added some horizontal pieces to the mix:
Left and Right connecting pieces
Top piece with horizontal pattern
One tile is all horizontal pattern
Gonna have to make a 2nd left/right connectors as the current ones don't line up with the vertical portion at all, yet fit well when combining two of the smaller roof tiles.
Hope that doesn't sound half as confusing as that was to type.

Anyway, need some feedback on some things. Does the new roof fit in from the attached screenshots? And the other old roof (the blue one), should it stay in or should I say "fuck that other roof" and use the space for other stuff?
Also, I want to redo the building parts of the houses, but haven't quite decided on a general design. Anyone got any suggestions? I'd feel like I'm half assing this if I didn't mess with the buildings themselves at this point lol.