I'm doing some second-guessing here, but it seems that you must get stormwater from the back yard to the front. Since the former french drain is non-functional, I'm wondering if you can change it to a slot-covered trough drain that collects water at the critical places and then directs it via underground pipe to an outlet somewhere toward the front yard... ?? Since you won't be hiring a hydraulic engineer, I would lean toward keeping it oversized... thinking about those big storms and the fact that drains tend to collect "stuff" and become clogged. 4" pipe is too small. 6" or a pair of them would be better. (If you can figure a way to keep it above ground, even better.) The exact details of how you constructed it would depend much on how the plan shapes up and what else you're constructing. Being as it's your own yard and your doing it on the cheap, you might even consider constructing a removable slotted grate made of treated wood. It wouldn't last like other materials, but you could get a few years out of it. In regards to planting on the hill, I'd be in favor of getting rid of all grass, thinking it's not fun to maintain, creating instead a solid small flowering tree canopy that would be limbed up with a high ceiling. Below it, a single, solid groundcover. Trees that come to mind would be redbud or saucer magnolia, with a preference for the former. 5 trees in a double staggered row (3 at back, 2 at front would do it.) A super cheap groundcover would be virginia creeper as you can find it everywhere and start your own cuttings. It's pest free and grows about 12" tall. You'd be able to incorporate other plants at edges, once some shade is up and running, and in the sunny areas.

Juliann, I'll post a site from the UK that has pictures of various types of gardens. This link goes to their Cottage Garden which they say is "contrived to look uncontrived". There are many other types of gardens there that might provide inspiration. Which plants you choose depends on which climate zone you are in. I'm in zone 3 so am somewhat limited in what I can grow. I'll post a pic of what I call my wild bird garden. It's an area in my large garden that has the birdfeeder and birdbath. I allow the flowers to go to seed for the birds so they self-seed. This area has changed over many years altho I initially seeded shasta daisies (the butterflies love them) and yarrow and planted a few established perennials. The yarrow seeds I planted were a mix of red, pink, and white, but the white resembles the wild yarrow we have so we pull it out and it's mostly now only tones of pinks and red. There are also Lamb's Ears because they seed all over my garden but I leave them in this wild area (the bees love them). There are a few other plants, a pink mallow that's 'weedy' but it fills the space and is quite pretty and we also have several lilacs here. Near that area there is also a drift of common old irises which we've allowed to spread. They are in the lower part of the rockery and I will eventually weed some of them out as the bloom time is not very long. If I were deliberately planting a wildflower garden I would not buy a wildflower mix as there could be invasive plants in it. I planted a mix about 14 years ago and still have Dame Hesperis (Dame's Rocket) altho pull out many every year and try to dead-head them ASAP before they seed. It's quite a weed in warmer climates. I would choose seeds of plants I like that are hardy but not invasive and mix them together. Another option is to plant in swaths with various plants and grasses hardy to your area. Keep in mind the moisture requirements of the plants as you decide. The area where I have shastas, mallow, and yarrow needs little watering and only a spring weeding so is easy care. Here is a link that might be useful: The Garden House

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.

Some thoughts on two projects: One: What is the most practical path from the point of origin at the house to get to your dock -- the path you now use ? Would that path begin at the corner of the house closest to the yard toys -- either a straight or curved path -- until you get to the toys and then from the toys beyond them to the dock? That walk path is where you should begin to create dirt steps about 4'-6' wide by using railroad ties strategically placed across the path as temporary small retaining walls to create level or gently sloping "steps" between the rail road ties -- digging to throw dirt above or below the railroad ties as needed. As you walk, you might take two or three steps on each dirt step you create. As you use the dirt steps you can see what steps work best and what steps need to be adjusted before you invest in blocks or stone for more permanent retaining walls for your grass covered dirt steps). Two: you might consider putting a retaining wall all along the lower point of the yard where you usually cease to mow -- below the hill. Literally dig a deep ditch for a footing/foundation along that line above which you cannot safely mow. You could then put rebar in place and have concrete poured into the ditch (BEFORE before you remove the dirt from below the ditch/concrete wall so the sides of the ditch can serve as a form for your retaining wall) -- before you throw any that dirt from below the ditch to above it. Once your poured concrete has set up, you can add a bock wall atop it, then begin to remove the dirt from below the concrete retaining wall to above the concrete retaining wall, adding other layers of concrete blocks to the wall as you are able to reach it from either above or below until you've achieved a reasonably level area both above and below the wall. You could then face the poured concrete with stone or brick if you choose.. DO make sure the bottom of the ditch you dig is lower that the ground level you want for the lower flatter area below the poured concrete retaining wall.. A ditch dug with a back hoe or other equipment will be wider that what you might dig by hand and take more concrete to fill but with the wider concrete wall you're pouring, you're building strength into your retaining wall. Do post some after pics to show us what you've done.