I don’t grow any of the OSO series but they would probably do fine for you. Take a look at the Easy Elegance roses too, I think Lowe’s has the best selection right now. Take a look at clematis for your trellis. Even if they die back to the ground they bounce right back. I think Weigel is too big for that space, and it does have a short bloom season.

I have a clematis growing in the back, and while it does look nice there it kind of lacks the drama for the front yard. I can probably just forego a trellis plant in that spot, or at least put that search on the backburner for now.

It looks like weigela comes in all different sizes, and the two varieties I mentioned seem small enough (Fine Wine and Roses and Wine - some are even smaller), but as you say, the shorter bloom season turns me off.

I will make sure to check out the Easy Elegance roses, too, though something I liked about Cherry Pie is it doesn't really have the "frilly" rose look.

I have reviewed your opening post, with special attention to the highlighted words.

Roses are not for you.

Would rock rose be appropriate in your zone? I like the crepe papery flowers and they are about as fuss free as any.

I just looked up some photos of rock roses and they do look pretty. They definitely fit my sort of Mediterranean vibe. However, it looks like rock roses are hardy only from zones 8-11, but I am in zone 5, which sadly eliminates a lot of beautiful choices. :( I saw a couple rock roses advertised as hardy to zone 6, which is still a touch warmer than here. I know some people "zone push," but I'm not sure if I'm bold enough to try that, especially for a plant that's meant to be the center of attention.

Hmm, the one I looked up did say z 6. Next to house might be a safe microclimate, but others may have better ideas for you.

Only the hardiest Cistus persevere in presentable condition through significant cold snaps in my part of USDA 8. So no way in Zones 5-6. Plus they aren't going to like eastern summer conditions - what they want is a Mediterranean climate, with mild rainy winters and arid summers.

I grow Weigela Wine and Roses and while the blooms are short lived the foliage is a beautiful dark wine color

It makes a lovely foundation plant but I would not want just that. I would want to mix it up with something that adds some more color.

Any suggestions on what I should pair with the weigela (or even the roses)? :) Maybe a front border of lavender and something else? Or something else completely? I saw that some weigela, including Wine and Roses, can see a second bloom if you prune after the first bloom. Has that been true in your experience? For the ones in my neighborhood, it seems like the second bloom is nominal - just a stray couple flowers here or there.

At this point, though, I still feel like I am leaning towards the roses. Probably still Cherry Pie, though there is another one called Oso Happy Candy Oh! that looks almost identical. And there's always Knock Out Shrub Rose, which is not my first choice, but I will go with whatever is the least dependent on me for its well-being and will perform best in the place I need it to be.

I am not sure if you can get the Shield Rose where you live. This one has survived everything that is thrown at it. I never got around to covering it up for the winter. due to going for therapy on a pulled muscle in my arm and upper thigh. I was afraid it had gone but like wow they all survived but one. Here is one of my Shield or there is the gorgeous Chinook Sunrise. Was having issues but you should see it this year and I never got to cover it up as well. This shield rose is awesome!!! Hah one lady said I should cut it back as I wouldn't get any roses on it. Well it made a liar out of her as it did indeed get roses on it all kinds of beautiful red ones. Even had a bout with the sawfly larvae which I ended up taking out my stool and a measuring cup of hot water and dish detergent and picking them off it by hand. Then when finished I threw the water over our wooden fence with them in it. :) I live north of Toronto in Ontario, Canada. Have yet to see the flowers on the chinook as they were all finished with for the season when I bought it from our nearby garden centre. But have seen pictures of them online. Have yet to see any buds on the shield or the chinook.

How big is that bed, measured from the landscape blocks to the house? It looks like the barberries are almost touching the house. So the bed faces the south, no shade, against a stone (brick?) wall which retains the heat, no air circulation, and planted under the roof overhang - perhaps the barberries are roasting and dying of thirst in their little microclimate. I suggest making the bed deeper by at least a couple of feet and pulling any planting out away from the house.

There is actually a couple feet between the bushes and the house and the overhang in that area is not substantial, unlike that which is over the hostas.

When I went to get my Lemon Drift rose from that Nursery on Monday they also had an Oso easy rose I think it was in pink!!! Couldn't buy two cart only holds one. And my main goal was to get a drift rose. Which they had 2 left. Sooo got one of them.

Landscape roses should he fine the Chicagoland area. Rose Rosette is not all that common there compared to other areas of the county. The Oso Easy roses are also very hardy and the right size for the bed you showed. Enjoy your new garden!