I think that solving the main problems is going to boil down to two things: the walk; and the making the entrance visible. The walk should definitely be wider - 5' could be a goal, maybe wider near the stoop - and then it should make a better connection with the drive. I don't think this means to necessarily cut across the lawn with it. Given that the yard is small, you could widen the drive a bit with whatever the walk material is, continue on by widening the city sidewalk with the same material, and then turn the corner with the walk, heading to the entrance ... in effect bordering the yard with a "U"-shape "invitation" that extends from the drive to the entrance. (The portions adjacent drive and city walk would not be the same width as the main walk to the entrance. They would be like decorative borders.) When it comes to the portion of walk that heads toward the entrance, I think it would be beneficial to pull it away from the neighbor's drive and incorporate and "S"-curve into it. That way, room for a SMALL tree could be created between the walk and neighbor's drive. It would also have the benefit of making it look like it belongs to your property without any question. Note how entrances are typically clearly marked by some type of enlarged, often raised, paved area, and a roofed covering that offers shelter from the elements. I think you need to create such a structure over the walk, in the front yard, near to the house. It would be the obvious first "entrance" that people reach when approaching the house. But after they've reached it there would be no question about where they would continue to in order to reach the actual house entrance. The structure could be a very nice arbor, or it could be more architectural in nature (such as with brick columns and an actual roof.) BTW, I don't think there's the first thing wrong with your yellow brick. Maybe you're bored of it and that is the driving force behind staining it. But I think it would be a mistake, or highly inefficient at the least, to attempt to change it to another color. If the brick was flat out ugly I'd be all for it. But it's not. You might end up creating, after spending a lot of money and effort, something that is not near as nice. If you could replace the top panel of the garage door with one that has windows all the way across, that would resolve the boring quality of the existing door. There seem to be two main approaches to planting: smother the house with hedges; and smother the house with a variety of all kinds of plants strewn in a randomish fashion. You might consider "matching" shrubs to windows (like steps would be "matched" to a door) as the main shrubs of the landscape scheme. Perennials and annuals can be fit around them in some artistic scheme, keeping it simple preferably. I would plan on keeping shrubs below the window sill height. I would hunt for a spot for another small tree at the right side of the house. (We can't see that area.)

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.

That front row of little pom poms needs to go too. Overall, the entry is squeezed between plantings--open it up--that is, widen the entry area for the full width of the little entry way--perhaps even widen the entire path if it's withing your budget. And the bed to the left of the walk should be at its widest at the corner of the house where a small tree would look nice.

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.