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.

I am with Dottie that you would do well to plant next fall (mid-September to late October in your zone) to allow root growth but have less stress on the plants due to shorter, cooler days. Regardless of what you plant, it will need regular water until the ground freezes. This season you can evaluate the site and plan so that you are ready come fall. I also agree with Dottie about voles - you could ask on the perennial forum or on the shrub forum (whatever type of plant you end up with) for suggestions that seem less attractive to voles. Most types of deodar cedar (Cedrus deodara) are hardy to zone 7, so not an option for you, though there are some types rated for colder temperatures such as 'Kashmir', 'Shalimar' and 'Polar Winter'. I'd check around at local garden centers, botanical gardens, and arboretums to see if anyone has local information as to how they do before planting them. It's tough having a borderline hardy tree that does well for several years and then is half-killed during a particularly cold winter. My inclination would be to plant native plants or ones that you are sure don't have escapist tendencies since you are on the edge woodlands, and plants such as ivy or vinca can grow into the woods, disrupting the native plants. You may find that you have already existing woodland spring wildflowers when you go into the woods in the spring. (Be aware that spring is the worst time for ticks, though they around all of the warm season, so get in the habit of doing a careful check of clothes whenever you have been out in the yard, and of your entire body at least once a day if you have been outside at all. It takes a few minutes, but I include it in my bedtime routine and haven't had an embedded tick yet, though I find them on my skin and clothes often.) Light levels: If you plant the slope with typical meadow wildflowers, you may have mixed results, depending on the amount of sun you have. Something like Rudbeckia is really a sun flower, and so may not do particularly well there. I would start taking photos at 8:00, 10, noon, 2, and 4:00. Do this at the spring solstice (mid-March, 1st day of spring), and about once a month up until the summer solstice (mid-June, 1st day of summer.) This will give you a good idea of how much sun you actually get there. If you want to try Rudbeckia, I'd go ahead and do that this spring since it will establish better with less established grass. By planting time, you may have a pretty good idea of how much sun the area gets. Water and nutrients: You might want to ID the trees along the top of the slope; depending on what you have, they may send out more or fewer shallow roots into the slope area to compete with whatever you plant. I say this because they look to me like red maples, which have fast-growing shallow roots and will compete for water and nutrients with whatever you plant. So the sooner you plant, the sooner what you plant gets established enough to be able to compete with the red maples. If you have oaks, they won't be an issue since their roots are deeper. Watch the slope and see how water levels fluctuate over the year. If it is a recently cut bank, the soil may actually be subsoil and benefit from adding organic matter to the surface, or there may be springs that will cause problems if not addressed. I'd also get a soil test done (Cornell U does them among other places) to see what will grow well in your soil. For instance, that might be a lovely place for some rhododendrons, but only if you have acid soil. Mowing: If you end up deciding to keep this meadow, it will need mowing 2-4 times a year with a brush mower to keep out woody plants. In my area those woodies include sweet fern, red maple, staghorn, sumac, white pine, black cherry, all of which like open areas for their seedlings. Seeds will blow in or be brought in by animals, and some of them will start growing, often including non-native invasives such as buckthorn, bittersweet, barberry, burning bush, and Japanese honeysuckle. In the northeast and Great Lakes area, unmowed areas will always turn into forest eventually, so you want to mow to prevent the process from getting started. In our field we time mowings to allow the ground-nesting birds' chicks to hatch undisturbed (turkeys are our most frequent ground nesters), and to allow certain plants to bloom, but for a chunk of time it is just mowed field. You can time one of your mowings for early fall just before the leaves change color, which will allow flower seeds to ripen but prevent baby trees from storing nutrients. Your landscaper may have access to a brush mower to do this for you. Regardless, the part you keep for sledding will need either regular mowed grass or the periodic Consider a mixed shrub border for the less steep part of the slope. I have one that is heavily mulched or groundcovers between plants and edged to keep out grass, and I only spend a few hours a year (perhaps an hour a month) weeding it, and it's probably about 15'x70'. It provides blooms, varied summer foliage, winter evergreens and berries, and colorful fall foliage for very little maintenance work. In the late fall or early spring I use hedge clippers to whack off the perennials and clematis to ground level. This one is full sun, but I have others in less than half day sun with a mix of shrubs and a few perennials, also edged and heavily mulched. This one is about 5 years old. Fall Spring early Winter So you have lots of options, but specific plant recommendations depend on your goals, your soil, and your sun levels.

"The large deck ... is structurally sound, the boards are not in good shape." What exactly does "not in good shape" mean? ... that the surface is not good but otherwise they are OK ...? That sounds like a couple of decks that came with a house I once owned. They were functional but ugly from years of weathering and no attention whatsoever. They were transformed into completely acceptable, nice actually, merely with pressure washing, a quick, coarse sanding, and two or three coats of deck paint (not stain) applied with a paint roller. It was not a huge, horrible job and they looked almost as good as new. They were much easier to keep clean with a hard paint surface. The cost to fix it this way, if DIY, would be a couple hundred bucks. If not DIY, a few hundred ... vs. $17K. If you could get another dozen years our of your deck and have it look nice, too, would that be acceptable? Landscaping is a discipline where one must not ignore site conditions or impose unrealistic solutions if they expect to produce a result that is pleasant, lasting and maintainable. I question the overall direction of making a small porch with steps down to where all the landscape features would be. This seems intrinsically less useful than would be having a decent sized deck immediately off of the main living space. I see a grill but not a dining table. Where does the outdoor dining happen? If the kitchen is separated from outdoor dining by a full flight of steps, it will surely be made much more inconvenient. But the real deal-breaker for me is the imposition of "no groundcover," which is driven by unrealistic beliefs based on emotion, when the site itself is demanding groundcover for practical reasons: there is slope and there is shade. Are we really going to spend $50K in order to change this into flat, sunny ground? It's going to require significant retaining walls & grading in addition to all the other new hardscape and planting. On the subject of husband's allergies to pine, I presume you're talking about allergies to pine pollen (since contact with the plant itself can be easily avoided)? Getting rid of the pines is going to make virtually no difference if there are other pines in the neighborhood or region. During the pollen season, which lasts for a couple of weeks, it can blow statewide and there's no escaping it. One's best hope of avoiding it is to stay indoors as much as possible during that time. I think you should begin with the budget because it will determine what is possible vs. what is fantasy. Re-contemplate the goals ... not how to achieve them, but simply the objectives themselves ... what activities do we want to do outside? How convenient do we want them to be? How private should it be? ... etc.

Yardvaark - wanted to make sure I understand - the "curb" you referred to is the U shaped red lines in the diagram which is essentially a border of wood and the swing set base would sit on top of this wood? I assume the U shaped red line wood border needs to be made level (by digging out a little dirt on the higher side of the yard)? 2. As simple as the proposed solution is (compared to the original idea), my husband & I for various reasons cannot do this ourselves. Do you know what type of contractor I should contact that can do the above and put the playset together at the same time? (don't think it can be done by 2 separate people at different times). (I don't know that landscape companies put together swing sets; landscape? handyman? etc) 3. What material can be placed under the swing set (definitely within the red U shaped lines - rectangular box and general area where the rockwall/ladder/slide touch the ground, behind the slide, etc)? (just thinking of alternatives to grass, having to mow in/around). Would I need anything to "contain" this material and if so, what? 4. I found this product on costco - a rubber border. Can this be used in my project or not a good idea/not applicable? https://www.costco.com/64'-rubberific-timber-playground-borders.product.100047336.html Thank you!