TVEyes - thanks for all this information and the workflow! That is great.
littlelostalien - the problem you are describing could come from sculpting the edges of the 3d plane while you have it tilted. There are a couple of solutions to that.
First, have the plane perpendicular to z axis of the canvas when sculpting the edges.
Second, turn on picker: once ori and use that when sculpting the edges. Keep in mind each brush stores this setting so you have to change it for each brush you use.
I hope this helps.
ryan