The problem with Sketchup is still the same as when it first came out. Modeling accurate terrain and incorporating with the architecture. Let me elaborate...
My last model was fun, until I had to set it into the landscape. The landscape was a severe grade with winding paths, platforms, stairs and driveways. The paths were integrated into the multiple stories of the structure and that meant the terrain had to meet the architecture precisely. At first there was no digital survey model and I could only use Google Earth. Google Earth is rudimentary at best and I only could supply a rough concept, tweaked and pulled for hours.
I searched for a way to use DEM data, but on a MAC it's impossible. Later when I did get the site survey I still had a hard time twisting the surfaces to mate with the model. I spent as long with the landscape getting it to work as I did building the structure that was to set into it.
Yes, I bought the book (You know the one I'm talking about) but it really fell short of what I needed. And I used every conceivable plug in and tool in sketchup.
For now, I'm going to have to refuse settle structures into there site landscapes. Until I can figure this one out.