The 2’ wide bed that currently holds a pruned-to-within-an-inch-of-it‘s-life hedge is much too narrow for most shrubs. The sidewalk looks super narrow too so obviously you’ll need to keep growth away from it. Unless you want to continually trim, I’d plant some flowering perennials, maybe 1 or 2 kinds, to fill that bed. Something with a narrow growing habit, 2’ tall or so.

I'd put the flowering tree, which I'd pick a dogwood, at the right corner of your house. Far enough away that the mature size fits. There are a bunch of native shrubs that should do well where your hedge is. Mountain Laurel is evergreen. As are some azaleas and most rhodos. You'll have to look for dwarf cultivars. Then you can add some evergreens of varying shapes.

Azaleas and rhododendrons *require* acidic soil. Do you have this? In Ohio, it isn't a given. I seem to remember the lilacs doing much, much better than the azaleas.

IME, cold winters, alkaline soil, and shade don't lend themselves to 'interesting', with the possible exception of mahonia.

I'd strongly recommend going slowly. Take your time about ripping things out, and have a plan first. Don't think this all has to be done in a year or two.

You do know where Bluestone is? I try to hit their sales when I visit my DD in Cleveland.

Thank you all for the comments so far- much appreciated. I did some checking when I got home and found that our soil is fairly alkaline. I also measured the strip between the house and pathway is 5.5’, not 2’ (seems my skill at estimating distances could be a little sharper. Haha). Hopefully that allows for some more options in that space.

I'd want the steps up to the door to be the same width as the walk. And I'd want that wider. The steps aren't level so they need fixing anyway.

Yes, the walk needs to be much wider, more attractive and the steps to the porch as wide as the porch end itself. With the alkaline soil eliminating many evergreen shrubs, you might consider using a groundcover with a little height to replace the dreadful hedge--perhaps Geranium macrorrhizum--pretty much evergreen, highly weed suppressing, highly deer resistant, good for shade to mostly shade, blooms in late spring and easy to manage/control.

You have a detached garage. The current entrance is more often accessed from the front of the porch. If you move the steps to the front your garden options expand dramatically. You can do a wider paver walk