You could incorporate the pond by adding some rocks with a bit of presence - groupings along the back curves. And not dinky rocks, something with some heft and shape but that won't overpower the size of the pond; and buried in a bit not to look plopped by some magical accident. Interplant the rocks with a few specimens that can handle a western exposure, but not sure what they would be in your zone. Dragon's Blood sedum is a low growing creeper, hens & chicks. An annual sweet potato vine could be trained into interesting cascades. All I know is when it comes to gardening/landscaping for the DIYer is that the heart knows what the heart wants. Most of us non professionals cut our teeth by trial and error; by pouring over gardening books before the advent of the internet; by skulking around local garden centers; by overplanting things that just weren't quite appropriate; by making mistakes and replacing failures until something actually worked; by realizing it's a plant and not "my baby" (as I so often see plants referred to on some of the forums) so it can be uprooted, discarded, replaced without trauma.

Scout, I bet it's beautiful, but you need to rip out the fabric. It will smother the roots of your plants and it doesn't allow for air or moisture to enter. Then, when you mulch on top of it, the weeds will germinate in the mulch, defeating the fabric's purpose. As a volunteer, I spent three weeks ripping it out of a public botanic garden's orchard here. It had smothered the roots of the trees and the Bermuda had gotten mixed up in the fabric and we couldn't get it out....UGH!! Here is a link that might be useful: Landscape Fabric Info

I think that my strategy would be to plant a few small trees rather than one large one, far enough from the fence so as to not get into the wires. If you put garden beds around the trees or more accurately put the trees within garden beds, she won't need to worry about mowing under them. As far as placement, put them where they will provide desired shade, but far enough from the fence and wires so that they won't cause issues. Exactly where that is will depend on how she uses the yard and the particular trees used. Does she want room for a dog to run or to sunbathe or a volleyball net or . . .? Is she planting a tall slim tree such as the columnar sweet gum Liquidambar styraciflua 'Slender Silhouette' or something shorter and broader? The Fox Valley river birch AKA Betula nigra 'Little King' could work for you. IME they drop a fair number of little twigs, but that they are fine enough so that they can be mowed over by the lawn mower. Fastigiate or columnar trees could be taller since they will grow narrower. There are a range of flowering crabs, and some are quite short and have quite small fruits that are readily eaten by the birds; the fruit that does drop I wouldn't consider a mess unless it was falling on pavement since they are small enough to disappear into the garden plants below. She would want to avoid larger fruited trees. You could also look at some of the larger shrubs and limb them up. Large panicled hydrangeas (H. paniculata) are often pruned to tree form, and some are large enough to form small trees. Look also at other large shrubs recommended for your area and research to see if they respond well to tree type pruning. Check out smaller Japanese maples for your area, especially some of the hardier species such as Acer japonica. Another alternative would be a trellis with tall vines such as Lonicera sempervirens, a native honeysuckle, growing on it. Here is a link to the USDA zone map. You can type in your daughter's zip code to get the zone, but generally Chicago is zone 5, either 5a or 5b.

I live in south Louisiana (Lafayette) and just started front landscaping. Any advice on layout and plant suggestions is greatly appreciated! House faces south/southeastly.