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.)

If you want a forward facing gable over your entry: remove the existing roof of your front porch. It can be replaced with a shed/half roof sloping away from the right exterior side of the house after you create your front porch with a forward facing gable. Enlarge and enclose the walls and flooring of your existing porch so the exterior wall on the side closest to the road is made even with the rest of the front exterior wall of the home. Beginning halfway between the downstairs right front window and the right front corner of the house, create a forward facing gable with a ridge point halfway between that beginning point and a point on the right that is as far right as needed to be even with the far right edge of the existing front porch. Your new front exterior wall of your new wall will be a continuation of your existing front exterior wall and the forward facing gable you create will cover your new 6' deep front porch. Your new entry door will be on the right half of that new front porch. Alternately, remove only the half of your existing porch roof that slopes away from the road and enlarge the walls of your existing porch as before -- to have the wall closest to the road be even with the exterior wall of the home now closest to the road. Then extend it the roof slope on the back upward to a new ridge point that will enable the slope that is on the road side of the house (of even length) to extend over your new front porch -- that will have a shed roof toward the road. Again, put your front entry door in the right side of the new front exterior wall of your new entry and create your gable roof facing the right side of your home. Then create your new sidewalk leading to your new front door. If there is room for a 4' - 6' front stoop between the front exterior wall of your home and the tree w/o harming the tree roots, the tree needn't be cut. Toward that end, you might use a treated deck board floor for your porch rather than dig a footing. As an alternative, you could use a flat roof for your new entry and create a deck that wraps a few feet around your right front corner. Edited to address tree issue and deck issue.

You’ve never seen it done nicely? Nope. It makes the front look pasted on like a movie set front. Be super careful of adding stucco. So much of it that I see is detailed incorrectly and let’s moisture into the building which isn’t obvious until there is substantial damage The builders suck at so many things they do in Florida. However getting stucco done well usually isn't one of them since it's so common. The majority of homes in S Florida are stucco.

As you probably already know, putting a window there would be the optimal thing to do. If you can't then maybe a large piece of outdoor wall art. When you paint the siding, don't reinstall the shutters. They are way too small and are inappropriate for this style window. You could beef up the trim around the window and that would help. Also, a color with a bit more depth would enhance the look. If you're interested in seeing some virtual makeovers of your home, check out my website, Creative Visual Concepts