I think the holly needs to be your target. It's blocking/crowding everything. For me, part of the beauty of dogwood is the trunk and your holly obscures it almost completely unless standing way back from it.
We have had monstrous, vicious hollies at every single house we have lived in that former owners just let go to do as they wished. They are aggressive plants and want to take over every inch of space available. We just arm ourselves with heavy long sleeved shirts, jeans and leather gloves. We use a bow saw, small chain saw if need be, and loppers. We have totally removed 15' round 5-point holly we couldn't stand to get near. We have cut back 2/3 growth off bushes over 12' in diameter and as tall.
They look really bare/ugly right after they are cut back, often just the central trunk left, but they shoot out really fast, too. Ours at this house, planted by a former owner, had to be cut off my driveway as well as the front flower bed it was planted beside because it was overtaking our best location for our city trash cans and blocking 1/3 of the front of my house. I did want to keep it, if only to hide the trash cans, so we decided to just cut that one back a lot (circled in yellow below). Two others to the right of this one (circled in red below) we totally took out as they completely blocked access to the window for cleaning.
As can be seen in the old photo above, all 3 hollies on the left of the entrance were very large. Photo below doesn't do justice to the size issue we faced. They were monsters!
We cut back severely to just the main hardwood trunks pretty much, with just leaves up at the top of branches. I figured if we killed it, I didn't care; if it lived, it would fill out to a more manageable size for future maintenance. It filled out in 2-4 weeks with new shoots popping out all up and down the bare trunks. It looks much better now from the street and doesn't hide 1/3 of the front of my house! Before the cut back, workmen wouldn't get near the thing to work on the house, electrical, gutters or roof in that area. Couldn't blame them........we wouldn't either!
I've circled the worst offender after cutback in this photo. Before cutback, it blocked the entire brick wall left of the window. (circled in this photo taken after our severe pruning)
I've just this spring planted two red Mandevilla on a trellis (below) that will fill this area in due time without trying to kill me when it is neared. For home security of this window (why the holly was installed there I'm sure), I've planted 5 1'-2' tall groundcover Meidiland White roses which I can get around much easier if I have to. They're not in this photo yet as they had not yet arrived.
I think once you cut the holly to a nice, respectable roundish considerably lower bush, the dogwood will show off nicer, the azaleas will be more visable and easier to shape. The bed on the other side, you can play around with until you get it the way you want. Clearly shade-loving plants will be needed there.