Funny. (Also in New England.) It's so true about not using our front doors, but in our experience buyers and their agents do proceed straight to the front door, despite what door they might use in their own home, or when visiting friends or family. We actually don't want them to come in the front door, as we think the initial impression from the side door is actually better in our case. Front is a center entry, with a central staircase in the house, but it's not a very functional entry... it's cramped and no place to put shoes. We put the lock box on the side door, but it's never used as our realtor has always attended showings. Our realtor thinks it is "off-putting" to redirect people away from the way they first attempt to enter (I disagree) so most people keep coming through the front. I agree with the sign ideas.

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.

An overall cleanup is in order first. I’d remove all plants/weeds/shrubs next to the house shown in these 2 pictures. And all the stuff on and around the steps by the yellow inset door. Then assess. I don’t understand what you said about the front door - the yellow inset door is not the front door? (By the way, that yellow-painted inset looks really odd, at least in these pictures. I’d paint it the same color as the rest of the house.)