There are a few ways to do this, I would draw the building separately temporarily making the 'basement' deeper than necessary, group it, then move it into position and Right click -> "Intersect with model".

Another way is to model the building and use the sandbox Stamp tool to stamp the building footprint into the terrain.[/quote]

Thanks! I'll give it a shot.

I have a question along the same lines, rather than opening a new thread I figure I'll just jump into this discussion.

After importing a terrain layer from Google Earth into SketchUp, how then do you draw ON the Terrain. For example. Say I want to build a series of buildings on a hillside, but I would prefer to connect the walls directly to the terrain, rather than connecting them below it. Is there any easy way to accomplish this?

Nice work!

I'm a novice trying to render my street. How did you get the scale nailed down? Did you have access to planning documents or did you just use the ruler in Google Earth to approximate everything?