Yeah, my little guy and our full time jobs have obv pretty much consumed all the hours since he was born not quite 2 years ago. lol...But, the pots I had started pre-him are actually all my gorgeous hostas that are just sprouting and now need homes ;_; The big pots are my hydrangeas that are coming out as well. I didn't want to put any into the ground since I wasn't sure of the plan for our yard. I would like to keep them potted and in our hopefully semi shaded new patio wherever that may be. The weeds on that upper part have been a struggle since day 1. The tree roots sprout new shoots constantly, so weed killer becomes difficult. Not to mention, the roses we had inherited with the property became diseased so we are in the midst of pulling them out as well. Believe it or not, we had a full vegetable garden year before last which is why I was hanging on to the empty pots as we do not have great soil. Long story short, I am looking to have more livilable space that doesn't include more weeding, watering, and gardening in our outrageously hot summers. If I put a patio in the corner between the windows and the retaining wall, what would be the best surface? raised wood type? Gravel ? would gravel hinder drainage and made the ground underneath even more soggy? same issues with brick? Even if I had concrete poured and connected it to the existing patio what kind of drainage solution would we need under and around? These are my beauties from last spring.

Have you considered paying to have a landscape design done? If you're comfortable paying to have the landscaping work done professionally, it might be worth the investment to have a plan put together. Potentially you could have them design phases if the complete design is too expensive for your inital budget. (A friend of mine did that: paid for a professional design with multiple phases to be completed over several years.) If it were my space, I'd want a nice big patio section with some kind of sun cover if possible. Love the pergolas with sliding shades that Oly posted. I really want one myself. Think about how you'd use a patio space (dining, lounging, cooking, etc). I would want some area for my dog to run around and catch a ball and a space for her to go to the bathroom. I think grass or groundcover are nice, but decomposed granite or bark would work too. I find rocks bigger than pebbles can get to sharp for her to run around on, so I wouldn't use that in any areas you want the dogs running around. I would also consider adding layers of trees and shrubs to bring life to the yard. They can be low maintenance and add a lot of beauty. If you can pick native species, that should help them thrive. I do think tiered landscapes can be very attractive, but I would want something with stairs to access higher levels. If you can afford it, rock retaining walls can look really nice but probably cost a lot.

Yes in your case would look odd cos you have already screen in porch with gable roof.

My nephew had 4 hunting dogs and 3 young kids and had his yard split in two. The dogs had one side and the kids had the other. The dogs were just too big and rough and knocked the kids over and it was easier to have two spaces. Nothing wrong with making the space work well for your family. It might look less awkward if the fence met the corner of the house instead of splitting the porch, but I am betting the old owners didn't want to have to take the dogs to the fenced in area, so they made it so the dogs could come out the back door and be contained in just part of the yard. What more do you want from your outdoor space? Do you like throwing parties, or having a bunch of kids over? How often do you use the outdoor space? Would you want a big outdoor kitchen area, extended patio space? Do you need to keep your dog contained? Would it be a PITA to have to walk the dog out to the fenced area rather than just opening the door? Do you have kids and do you want them contained? Do you have any plans for a pool? Maybe you can use the current fencing but just reconfigure it, If you extend the patio/seating area out another 12' and create gardens outside of the fence it will feel like you are keeping people from walking through the gardens and guiding them to the yard through the gates.