This is the 1st of several drawings on this very complicated piece of property. I am going to go through the series of drawings and rehash conversations with the homeowner.
1st problem was how to lower the drive to get into garages-especially the garage door on the right. Tight angle and tough slope. This discrepancy led to a lot of the drive needing to be lowered-which in turn now leads to the need for retaining walls.
My look at how I would landscape after the lowering of the drive:
[Looking down drive to parking area, garages and view down left side.]
[3rd attempt at getting a “look” for the entry to parking/garages. ]
Walls needed on both sides, some higher landscaping on right to block the house-somewhat. The old mystery factor.
Paved of course, maybe some detail in the edging. Brick walls, maybe segmented modular block. There has even been talk of making the left side(in the picture’s) a boulder wall . . . this leads to the discussion-“did we run out of money look?”. My guess is the boulders will not go in.
I also made an attempt here to show some detail to the entry into the private area on the left side, leading away from the more public(driveway/parking) area. This gate/fencing/arbor will need to be shown in greater detail-but is okay for conceptual drawings . . . to see where the client really is in his/her thinking.
More of the public/private separation . . . philosophy/drawings in the next post.
The Whispering Crane Institute 
Wow, thank you for this. I’m not nearly in the league of this drawing (either in size or slope), but the more I read you, the more inspired I get to do something with this jungle that I laughingly call a yard. Keep posting, please!