Alan,

That link is diffinitely something. Gives a few possible techniques to try. Tho the one of the main things I was trying to do, was to have the plain and street layout be created by the tool as well. One less thing for the user to have to do. Tho, I think my mind was going for the hardest but best outcome.

The boolean idea was going alright. The only problem is that many times using a boolean on a polygon causes there to be no resulting shape, although the outliner says there is one. The shape dissappears and contains no information. It would be easier if it the amount of times a boolean is done on the object wasn't so random. Sometimes it dissappears after one try, others it can range up 8 or 10.

The only reason why I was thinking about using verts to palce the buildings down, was by using to the pointPosition command to get the exact location of the vert in world space so that I could place the building exactly there.