If that photo is representative of the area in question, then I'd reconsider using this extremely tight space for "outdoor living". And unless I am missing something, that slope is not very severe. Even if leveled, I doubt this area would be congenial to lounging outdoors or utilizing as a patio, etc. Too exposed and too restrictive and without sufficient space to develop any kind of green privacy screening. I'd consider just a mixed shrub buffer between you and the neighboring property, perhaps with a meandering pathway connecting it to more usable areas of your property. Unless that photo doesn't reveal the true slope of the area, I'd say no terracing or retaining walls are necessary or even practical. Can you post photos of other areas of your garden that may be more conducive to outdoor living/entertaining? I still think this is a situation where engaging a professional for an hour or two can be helpful - it is difficult even from the photo to get a good visual and a true sense of exactly what you are dealing with.

The retaining walls are a bear of a project. That's something I would hire out if possible. I would first get copies of local building laws (state, county and municipal) for the retaining walls since you wouldn't want a telephone call from a neighbor to undo your work and since the saftety part of such laws is for your benefit. I know there are formulas for designing the walls but can't say offhand what they are. From the photos it looks like the slopes are a bit steep so a series of terraced walls would probably look and work better. If you do a series of terraced walls then you can plant up the terraces with plants that are not too heavy such as flowers or small shrubs. I would be hesitant to plant trees in terraces. From the photos it looks like the area gets a good amount of sun exposure so sun loving flowers might work. Some sort of interlocking block product might be good for the retaining walls since you can go at your own pace (one block at a time over several days if necessary) after the prep-work is done and since such walls are less likely to fail from heaving or from excess water buildup. Wood ties are probably easier and less expensive but will rot eventually. I'm guessing that the path to the pool will be paved or stone or whatever since you don't want to track mud into the pool or the house. A grated-covered drain near where the path meets the pool patio might be good so that water flowing off of the path during rains will not make a mud pit right near the pool patio. The path should be graded to slope down away from the house of course. I would also suggest observing the area during and after a good sized rain to see what drainage issues in the area might need to be addressed. Attached is a link to erosion control magazine which you can read and search for free online to get ideas and to find out suppliers of products. Here is a link that might be useful: erosion control magazine

Inspiration photo showing tall groundcover around tree. We just tapered the asphalt to help direct stormwater to its sewer and are doing some backfilling. The area gets occasional stormwater, but is fairly dry. clay. zone 6. I am trying to plan the area to the left of the stairs. I like the idea of breaking up the area with a light airy tree or shrub (red twig dogwood?) or tall grass, surrounded by a rectangle of a taller groundcover centered in front of the balconies. And then and then a workhorse low viney ground for the balance. What about a border next to the parking lot and next to the stairs - salt tolerant. wild geranium? wild onion? canada anemone? giant liriope? 1-3 ft sedge? The area does not need shade and I'm a little afraid of getting back to my BEFORE pictures. Doom. leaves. debris. Drawn to scale - each block is 5 ft. The sloped section of the leftmost rectangle where I am starting is 15ft x 50ft. Stars are existing shrubs, trees. Any suggestions? Thank you for reading

Don't build a retaining wall in the right of way of the road. I would suggest leaving additional footage so that if in the future there's some excavation there's a buffer for construction equipment. In my area on residential streets the right of way is 50 feet. So it would extend 25 feet from the center of the road. I'd add a few feet to that. I've seen slopes next to a sidewalk that were maybe a 25% slope. So instead of a wall you might use a mulched steep slope with some evergreen ground cover. Then leave the top fairly level back to the house. This way you might wind up with more level ground above the slope than you'd get with a wall recessed back away from the right of way. Don't put grass on the slope. In wet weather mowers will slide and tear up the lawn. And someone might get hurt.