I apologize, I tried to edit the post so it was a little more comprehensive and I ran out of time.

Also I live in south eastern Wisconsin.

Your honesty about the picture was refreshing. Many people try to avoid posting a picture only to confess when they must that they are embarrassed about something or other in it. For the most part, those of us who dish out advice could care less about any mess. We care more that we can see the essentials (house, hardscape, major trees, etc.)

We can't see some of the details of hardscape. The walls look like they might be incomplete. Where they turn back into the grade, they should extend all the way to it such that during a rain, water is not washing out at the back ends of the wall. If it is, eventually, it's going to be an erosion/maintenance problem. The tiers look OK appearance-wise. But the top of wall surrounding the steps is another matter. The sawtooth top edge has a look of being permanently under construction. It needs level portions with periodic step-downs, or simply to have a cap of uniform angle, like a ramp which terminates as some kind of an aesthetically pleasing abutment, or at least just covers it. (A planting that drapes over the edge would do that.)

But I think your question is mainly about planting. In sorting through the problem, I would cast aside until later your list of plants. Instead of thinking about any specific plants, thing about a scheme that would unify the scene. In spite of the fact that you want a lot of variety, I think you'll need a single, low groundcover that links all the disparate plants such that there is unification. Not sure what that GC would be in your zone but it would need to accept the soil and light conditions, and be dependable .... not something that might work if only the planets would line up properly. Though you want variety, there will need to be simplicity integrated into the scene in order that it doesn't look like a jumble. Once you develop a scene that is along the lines of your view, you can begin to ask yourself what plants will create the shapes, sizes and placement that make up the scene. There will be "massaging." (In my scene here, I'm keeping the larger plants toward the back half of the scene and letting the groundcover "lawn" stay relatively unobstructed toward the front.

Needs more than a little dribble or fringe of trailing plants to make all that wall-stone so it does not dominate the scene. Creeping kinds of junipers, maybe some bear-berry (if that grows there)...

Doesn't need a tree limbed up (stripped) so it looks like it was heavily attacked by deer, or a matching pair of anything (house facade is not geometrically symmetric).

(uploaded more photos below)

@Yardvaark

I agree on many accounts.

I need some sort of uniformity. I was hoping waves of hardy shrubs like the potentillas would help that. Maybe I'm wrong though.

I've started on planting things at the edges that would cascade over that massive stair wall. Sedums and creeping thyme so far. I've been eyeing creeping junipers but I haven't gotten the courage to put one in yet.

I wanted to keep some variety only because I read it is better for disease and pests control.

@ Embothrium, I agree. It's going to take a lot of trailing. working on it. :-/

yes, I wanted bear berry! Had my heart set on it for a while but it seems the soil too alkaline for it.

Took a few images in between the rain just now.. Again keep in mind this is mid mess and construction.

Also picking up some more large boulders soon to help fill in a bit more and have some plants creeping down from that.

weigela, spirea on the top tier, along with some little plugs I put in last year just to see what would grow.

limelight hydranea, spirea and mr bowling ball, along with some sedum and creeping thyme ground cover. Thinking its too dry here for the shrubs.

some ideas:

Think evergreens. Lots and lots of evergreens, since otherwise it is going to look drab and naked for much of the year. The spruce actually helped by drawing the eye up to the house, and by being there all year round. so start with what it is going to look like in winter - groundcover junipers, maybe a dwarf fir, or arborvitae. After you've done that, then you can start filling in the gaps with deciduous flowering shrubs. Unfortunately, given the narrowness of the lower bed, there may not be room for much besides the cascading evergreens there.There is distinct tendency among midwesterners to insist on arranging plants in rows or symmetrically or in some other pattern. You really don't want to do that here. (there is also a tendency to think that retaining walls are an automatic solution to all gardening problems, but I won't comment on that)

Thanks Dig Doug's Designs(8A). SO really likes the grass touch. We might not have enough space for the spread of a lot of these tall grasses. Doing some research now on that and which ones are invasive or not.

"The spruce actually helped by drawing the eye up to the house, and by being there all year round. so start with what it is going to look like in winter."

After the spruce in the back fell from a winter storm, We had a couple different pro arborist come out to see the Colorado spruce in the front before we had a repeat. It was all dead on the inside which is why it was sagging. It was causing problems. It should never of been planted in clay soil and humidity or so close to the house IMO.

We do want to replace it with another large shrub or tree as soon as the stump is out.

"Think evergreens. Lots and lots of evergreens"

Yes I would like some. Sorry for not stating it clear enough on my end, I am interested in adding evergreens like junipers but before I invest in a mass evergreen planting, I was trying to get an idea of a plan for them. To be rank, too many evergreens around here look like hell. I do like the way they look when done well.

"(there is also a tendency to think that retaining walls are an automatic solution to all gardening problems, but I won't comment on that)"

Thanks for the comment on the retaining walls. The retaining walls were a call to make for safety more then a perfect solution to all garden problems. The less slope to have to mow or weed, the better for us. I'm not as nimble as I use to be. The areas also don't get as dry anymore. It's not perfect by far, but it was what we decided on among the options.

We are doing the best we can here man. There will be no perfect solution, we know this. :-/

Dig Doug's Designs

do you think the taller corn flowers might look OK like that? The grasses all get to wide or aggressive for that area. I do like the height there if possible.

Hamelin Dwarf Fountain Grass is not large or aggressive. You might consider Nepeta in its place.

thank you.

I was also checking out Feather reed grass. that is stated to be tall but sterile and compact.

Nepeta also reminds me of maybe russian sage too.

I think it's correct. Evergreens would be an asset for interest and probably even the eco system. I need to get over my shyness about them and just figure out a place for some.

Thanks for the update.

tj

There are a lot of smaller evergreens that could be a foundation planting. Some very nice dwarf white pines for example, or even a dwarf Japanese pine if you want to go spendy . . . Smaller yews since you don't have deer. Gorgeous weeping dwarf hemlocks . . . The ubiquitous blue spruce not a good idea in a damper climate like WI, very susceptible to disease. Some gorgeous weeping options though. Almost every evergreen has a smaller and/or weeping form, but not available in common big box stores, have to go to a nursery specializing in them . . .

I this spring Id like to pick up some of those creeping conifers to cascade over the wall. We'll go to a local nursery either way. Thank you.

Stein’s usually has small ‘Mother Lode’ junipers for about $10 around Mother’s Day .

tj

Really looking good!

debra