I'm in Virginia. Are you sure there's been no rain? It can be pouring like crazy five minutes down the road and I don't get a drop, and vice versa. Plus, from my experience here in Virginia for 7 years, the fall is our rainy season. We get a lot of rain this time of year. It's raining right now. It's also very hilly here in Virginia and like I think it was LuAnnPA who said it--it's the norm and if you ruled out properties because they are downhill, you're ruling out a lot of good properties. The last place I lived in was downhill and that basement was bone dry. The property actually stayed wetter than where I am now but that's because we were in a holler and surrounded by trees so got little sun and wind. But it was never a problem. Just took a little longer to dry. Ask them when they had rain last. Ask them why it's wet! Actually, now that I'm remembering, our barn here is a little low and during heavy rains, a stream would go down the middle. Hubby just dug a ditch around the barn and diverted it away, filled it with yellow pebbles, and in five years we've never had a problem. I encourage you because that house looks beautiful.

I'm always going to plug finding a local landscape designer, but especially here because we just did a similar project. Every contractor who came in was advocating 8 ft walls and craziness, and we did it with two 30" walls and actually created a stronger transition to get their kid into the wooded area to play. Search for a local pro, there's a button for that above. Even if you DIY it, it'll give you some guidance. To your questions: 1- you'll have a lot more options if you lose the pines, unless you're willing to bring the wall well in front of them. In that case, I don't know how much value you get from the process. 2- it's worth checking with your city or county. There may be specific regs in your area that deal w/ disturbance of soil within XXX feet of a waterway. It may be as simple as you being required to but up silt fence, but cheaper to know in advance. 3- that decision would be site specific (for example, prevailing winds) as well as specific to the type and construction of wall. 4- I've seen plenty of DIY walls. Some are pro quality, some are horrifying, some are in between. Once you control for the variable of relevant experience, it seems to come down to patience, attention to detail, willingness to seek advice, and willingness to see something that went wonky and tear it out and redo. If you've done a brick patio you'll have some of the basic skills for wall building under your belt. You can square up corners, you can level an area, etc. Grading just comes down to only using the biggest tool you can confidently use. I have guys who work for me who can use a bobcat to feather out a nearly perfect finished grade that only needs a bare minimum amount of raking. I'd end up taking out a car-sized chunk of hill, so I need to do it by hand (which is why I'm management). We're in VA so we usethis typical details packet as a starting reference for walls that don't require engineering. Note that if you were to use a segmental retaining wall (as in the interlocking concrete blocks by companies like Techo-Bloc and New Line), most municipalities don't have typical details as in the above. If your wall will require a permit and you use a segmental wall product, you'll need to get an engineer's stamp. You have an interesting project, and I think bringing in a design pro would be hugely helpful. Yard brings up a great point in his comment, that you have a terrific opportunity to create a blend between more structured space and the woods beyond. I'd love to see that developed, for sure.

You don't level the dirt. You level the gravel/base layer. The bible for installation instructions isn't anything that gets said here. It is the installation instructions that come with the material you are using. You don't build the wall on top of the paving. The wall requires different subsurface prep, as well as being level. Paving shouldn't be level, since a slight slope is required for drainage. You build the wall, then install the paving up against it. If you really, really want to play with a laser level, get one and play with it. However, IME, a large liquid level is easier to use since it does a better job of behaving like the pavers.

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!