Me too Ascension. The only thing that strikes me strange is the buildings with the hip roofs that have a dark line down the spine which extends out over the hip. Are you trying to disguise the fact that the roofs are hipped? If so, there are pretty straight-forward ways to use PS bevels and eliminate the hips if you want a simple roof.

Draw a rectangle in black on a separate layer. I do these up and down, although side to side works as well. Make sure the rectangle is somewhat longer than you actually need. It can be a lot longer if you wish, just to be sure.

Next, give the layer a layer pattern of whatever roof pattern you want to use and scale it properly.

Now, create a new, blank layer. I do this just below the layer I'm working on. Select both, then right-click and merge the two layers. This makes the roof pattern permanent instead of a layer properly.

Now give the roof a bevel of about 50%, chisel soft, and as many pixels as it takes to bring it to a peak. For the highlight color I will use a lighter shade of the general roof color, and for the shadow a darker. This keeps the highlights from seeming overly harsh and keeps the building from looking too plastic.

At this point, I'll usually make copies of the layer for all of the buildings I plan to make in that roof style in that section of town.

Next, take your building and position at the correct angle to what you want to use. The polygonal lasso will work well for working with building when there are multiple buildings on a layer. Your building should now have the correct shading on the bevel for whatever your global lighting is. Once that building (or all the buildings on the layer if there are more) is at the right angle, create a blank layer beneath your layer again and merge them. This fixes the bevel and shading permanently on the building.

Now you can take you polygonal lasso and trim off the hips from the ends of the building. Now you have a classic simple roof with no hips and perfectly correct shading for a roof at that angle and a 22.5 degree pitch.

It takes longer than just throwing down a polygon with a bevel, but it is more convincing overall, and your roof textures will look more convincing.