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Not really sure of your intent with this area, nor am I really sure of your location, but I'm guessing your south of NY because last Wed it was pouring up here..
Also, I'm not a landscaper, nor do I play one on TV.
I like the octagon deck idea. I would make it fairly large, wrap it around the back of the house. Put one set of stairs to your walkway, & one into the backyard.
It would be easier to dream if I could see the area to the left of where the cat is standing in the first pic.
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