I would recommend that you frame the door with two taller pots, like these in the 30" height (https://www.potsplantersandmore.com/collections/outdoor-planters/products/corry-cylinder-indoor-and-outdoor-vase-planter?variant=14015347078) in a saturated color; depending on your tastes something like the cobalt, key lime, or matador red. In the area that is currently bark, I would recommend using round up on a cooler day (roundup does not work if it is too hot, aim for 85 degrees or below) to get rid of the oxalis. I would then recommend planting 3 Skywalker or Graham Blandy Boxwoods along that wall to bring some evergreen color up the house. Around the base of them, I would plant some Ice Dance Carex which is variegated and will bring some light to the area. Two other small things that could help update that area would be to use edgers that do not have a scalloped edge. Having edgers that only rise about 1-1.5" out of the ground with a flat top will give a more contemporary look. The other update, which would need approval and collaboration with your neighbor, would be to decide on a universal color for the fence. A neutral blue-grey color helps move the eye up into the skyline, making your space appear larger.

A pergola is lovely in a place with lots and lots of sun. Elsewhere, it can get dark and dank in the winter. I'd make a path to your door. Much of it can be part of your driveway. Just replace with brick or pavers or something visual that you can still drive on. Then, I'd clear out the shrubs along the side of the house with the door. I'd turn the bed by the right front of the house into a semi-circle no larger than the width of the house and have a variety of plants and heights instead of that yew hedge. (Not sure it's yew, but it looks like it). Window boxes are hard to keep looking nice. They don't have a huge amount of space for roots, keeping them watered enough but not soggy can be a challenge. This is why you see a lot more window boxes in carefully staged Houzz photos than in real life.

As mentioned, by nature of the architecture, there are few places to put plants against the house at this front face. The overhang plus the lower windows does not invite foundation planting at that area. A large planter could go in front of the wall just right of the large window set. A shrub at left of the left house corner could help establish a better setting so one's view doesn't run directly off the house to what's across the street. (Maybe there are some plantings at the left side of house that can help with this, too.) Other than that, some large, circular beds around the two major trees could help give some fullness to the overall look and a sense of the patio space being more protected from the public space. The height of that groundcover could be as much as 3'+ to as little as 8", with the taller giving a more protected look. There is some opportunity for colorful seasonal blooming depending on what plants you use. My suggestions are for layout and arrangement. Plants have to be chosen from what works well in your locale. I got rid of the tall evergreen left of the door. It seems overwhelming to the porch/entrance space, IMO. To clean up the overall picture more, I'd get rid of large-tree foliage that hangs low enough to shroud the roof. This might mean hanging limbs/branches, or removing some lower branches entirely. (It is apparent at the tree at the left that some branches should have been removed way back when the tree was young ... before these turned into a major part of the trunk system and are not hard to remove without removing a lot of canopy with them.) The grass looks pretty healthy in spite of the shade. It's hard to tell if there is enough hill to warrant complaints by the grass-cutter. If it's tolerable, I'd leave as grass. Later though, since there are more trees on the way, shade could become too much and warrant conversion of those areas to groundcover. I like the house colors and think they are well suited so wouldn't change anything there.

Appreciate all this feedback as our house has been a work in progress for last 15yrs. Was an ugly orange one-tone brick that we painted when purchased and repainted about 3yrs ago off-white with same color trim. There were sage green shutters on all the windows that were rotted and removed. We couldn’t afford to replace at the time. Should we add them back in updated style? We put a new roof on last year and went with brown tones. I like the idea of a darker trim color and maybe even a dark gutters. We’ve struggled with the lawn due to heavy shade and drainage issues. Our House sits below street level on the right side. Two years ago we removed one lg oak that was also on the right-side and limbed up all the other tree. We are considering sodding the entire front yard and tearing out the front walkway to the street we don’t really use it-we live on a really busy street. We moved our mailbox to the side street years ago and added a friends entrance w/porch with a walkway from the street. If we tear out the walkway from street straight to the front door we would replace it with a walkway from the friends entry porch around The house to the front door In front of a landscaped bed along the front foundation. I would say that I’m looking for an overall cottage-look. Im a very visual person so your drawings and pics are VERY helpful!