I do LOVE the raised creamy white brick borders around the front garden beds -- and would continue with that theme -- perhaps a long garden (with the same kind of brick borders) that would follow the line of the driveway? At the bottom of the driveway -- add a larger garden with a black lantern. Add a sign with your house numbers to the lantern post. Also -- get a black metal sign that would simply stick into the ground in front of the gardens on the right-hand side of the front door. The numbers should be pewter --on the black painted metal signs. Perhaps add a tall clean-lined fountain for the blank wall area between the two windows on the left-hand side of the front door. OR -- perhaps add a very tall shaped rocket juniper or perhaps a trellised or espalliered tree. Then add a couple of tall bushes or even trees (check for height and growth patterns of course!) for each end of that same area. Add large black wrought-iron lanterns above each of the garage doors. Then add a matching hanging lantern above the front door. Add a large pewter door knocker to the door itself. Add large clean-lined cream-colored containers on each flat area in front of the columns. Fill each container with a tall bush or ornamental grasses. Here is a link that might be useful: lamps plus -- example of wall fountain

I don't think the windows need shutters. IMHO, it's a very cute house and the cinder-brick screen is a lovely feature to highlight. Start by cleaning the bricks and the exterior. If you avoid painting those it will be a lower-maintenance exterior. Do paint the garage door a color that helps it disappear. If you want to paint the cinder bricks, choose something that highlights them. I like YVs design, it's very low-maintenance.

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.)

When it comes to something like first impressions I think opinions vary due to geography and age of the viewer. I don't know where you are so my old lady from California ideas may not appeal to you. I think the path is quite charming and would not want it partially hidden by the front bed bordering it. I would plant grass there. I think the railing looks like a jail on such a small house. I would remove it. The shrubs in the stone planter look to me like what I consider foundation plants. I suspect they will grow too large there. I would remove them. Perhaps they can go on the side of the house that is not visible. I would plant low perennials and leave room for annuals in the planters. I like the suggestion of green trim above except it looks like you may have a blue roof. If that is so I would stay with white trim. I threw in some little plants with red foliage in front of the porch. I like them with the brick. Lighting around the path would be nice since one of you is handy.