@goosemonger: I suspect that the odd perspective is because it's for
this contest. Correct me if I'm wrong, Huge.
Now for the art:
-The art looks pretty nice; I especially like the grass and stone tiles. You may want to increase contrast, or even add more detail, on some of the brick tiles, especially the front of the barbershop.
-Speaking of the barbershop, the perspective on that is off, if it is intended to have a gabled roof. If it's intended to have a different roof, feel free to ignore this next comment.
To draw a roof in perspective, especially in a funky one like this, several steps are necessary. I started with a simple box onto which I plan to put the roof. I then marked the center of the gable face and drew a line up to where the ridge should go. I then connected that to the box, removed the guidelines, copied the gable to the other side, and cleaned up. The next step would be to divide it into tiles, texture it, and so on. (Please note: when I drew this, I was not thinking about tiling. If it were intended to be tiled, I would have used much cleaner dimensions.)
-You may want to consider removing the black lines at the base of the barbershop and around the door. They detract from the image a bit. The ground line could be easily removed or even just replaced with the interior detail color from that face of the building.
-The buildings seem like they're floating. I don't know how you're doing on tile count, but you may want to consider adding shadow tiles. They might help in holding the buildings down.
Overall, this is a pretty nice tileset. You've done a very good job at getting a lot of details into 40 tiles, which is commendable. Good luck in the contest!