Prairie Moon has two Living Fence collections. I would select one of those. These super tall plants are similar to sunflower where is a single stem. I would look at one of those plants or plant sunflower. The edible sunflower are beautiful and would fit your needs but are annuals. There are native perennial sunflowers as well.
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That's an interesting collection. I think I've previously looked at three of the six. I'll give them another look. If I had the space for it I'd love to do a naturalized patch like they describe. I've also looked at sunflowers but, like you say, they are annuals and it's a pretty windy spot and they're vulnerable to wind damage. I've seriously considered false sunflowers I'm just concerned that they wouldn't get as tall as I'd like.
I have some false sunflowers in my hell strip by my ally. It gets pretty tall around 6 ft but not as tall as some of the living fences.
You could do the perennial sunflowers. I think the Maximilian Sunflower is recommended because it's doesn't spread as much. But I don't have one
Some of the dwarf varieties available from Mr. maple are wild (not just maples) so it could be a good option for trees, especially if you just put one in a very nice pot instead of planting it directly anyways. You can actually get trailing nasturtium to climb rather well so that could be a good option too.
There’s also some dwarf trumpet vines I’ve seen that should stay compact enough as well, but make sure you don’t plant the full size ones unless you enjoy constant pruning. I cut my (wild? It’s outlived the memory of anyone near this house at least) trumpet vine to the ground every year and they still start climbing the roof by the end of the year.
It’s probably not that terrible honestly, I just have asbestos shingles on my house so it gives me anxiety watching the vines yearning for them.
I had looked at trumpet vines but was concerned about how big it grows. I hadn't run across a dwarf variety. Summer Jazz Sunrise Gold looks really good.
My local nursery recommended a particular variety of buckthorn as a tall, skinny option. They are in the size range you're looking for. Pictures and info:
https://www.wilsonbrosgardens.com/rhamnus-frangula-fine-line-fernleaf-buckthorn-2g.html
I like the featheriness. I think that would look good there and maybe a thicker plant like that would convince the birds to nest in the plant instead of the awning.
I mean, if you want color, scent, and a long bloom time, you could go with a rebooming rose, like Scentimental or one of the Knock Out types. Most good rebloomers aren’t quite as tall as you were hoping for, although sometimes you can find them grown as standards.
There’s also lilacs, which even though you’d get only a short bloom, you could prune to whatever look you wanted.
If you want to just do a green dramatic accent, Ilex ‘Sky Pencil’ fits every other one of your requirements.
Probably the best tree that roughly fits what you want is Caragana arborescens ‘Pendula’. Not a rebloomer, but pretty flowers, a nice weeping habit, and a pretty yellow fall color do give it year-round interest.
I like holly the red berries look nice through snow. The weeping pea is also interesting, I haven't seen that before. It doesn't need to rebloom if there's fruit, fruit is visually interesting too.
Japanese Holly actually gets small purple-black berries (assuming a male nearby). Still good for birds though.
The peashrub can set a sort of tan fruit; but after flowering what people usually enjoy is the weeping form, pruning it to be more open to show that off (it’ll end up looking sort of like a snuffleupagus if you don’t prune). ‘Walker’ is a variety with more delicate foliage so it shows the weeping habit better.
Maybe a fuschia? There's a hardy variety if necessary
Edit:I misread your size request, but take a look anyways. I'd probably do a fruit tree or something. There's also a hardy kiwi vine you could grow on a trellis
The fuschia looks nice. Not what I'm looking for but pretty. Hardy kiwi is an interesting suggestion. It looks like the Issai cultivar is a little less aggressive of a grower and self pollinates so I could get fruit with one plant. Definitely one to consider. Thanks for the suggestions.