Gorgeous house. I think I would have it re-contoured so that it is flat on the portion of the hill next to the stairs. Add a retaining wall using the big rocks you already have from the bottom. It would be nice to have a retaining wall that curves from the stairs to the grass and make it low enough to double as a place to sit. You will probably need a second retaining wall at a higher level or have some of the dirt removed. The area would look great landscaped with flowering shrubs and flowers.

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I think match the stone on the walkway with the new flat area.

Analysis first, then plan.

What do you want the planting to do for you? Do you want it to look nice for your neighbors beyond, or for your guests above? Do you want to screen undesirable views? Do you want to want to block incoming breezes or welcome them? Do you want the sounds of a bubbler or waterfall from below? Do you want to attract birds, butterflies,.............. deer?

Are there any utilities buried beneath the bed, - electric, water or irrigation? Have you dug down along the walls to see where the foundation is for the walls- where the brick or stone begins its climb? That is where the original intent was for the plant bed. Why not respect the original design ideas.

Now you can develop your planting plans.

[For my benefit, could you radius that hard corner of boulders aimed at all the neighbors headed at your lower door, and just put groundcovers and bulbs in the space remaining? I would appreciate this more welcoming approach. Thank you.]

How much work/maintenance do you want to invest? The easiest would be to plant an aggressive ground cover, like creeping phlox...flowers all season and stays green through cold weather, drapes over the rocks.

At the other end of the work spectrum, you can design/have designed a rock garden with, perhaps a water feature, that would require some gardening every year.

Lovely.