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.)

There is a smothering feel that comes from having the first floor wall portion of the house mostly covered with foliage. Raise the canopy of any trees and keep shrubs from coming above windows, or too high up on the house. The bed should be deep enough that plants can be positioned to grow in all directions. (Usually, the bed is too shallow, plants are placed next to house and can only grow forward, in the direction of the street.) Use a shrub below the windows for permanent foliage, a perennial for some seasonal interest and some annuals for ongoing color. In addition to the walk, the shape of the bed can indicate, and reinforce where the entrance might be ... even if it cannot be seen immediately. The condition of the grass is even more important in a small lawn where it is seen from relatively nearby. If it is blemished, it diminishes the look of everything else. So work to get it into good condition. My picture shows a scheme. The plants you choose and their colors would provide the actual personality. If you use a fairly large shrub in order to create a small tree, and it has a limited height, you don't need to worry about it getting too tall, You only need to trim off the lower limbs and branches as it grows, which is easy to do and infrequent. Thus, it's lower maintenance.

Biggest bang for buck is to make a wide and welcoming path from the driveway to the front door, one that can be seen from the street. It will fill in the blanks for the eye. Your current walk is pinched up against the house and does not look welcoming. Quick and dirty, hide the hose in a decorative pot or wheel it around the corner or into the garage and just take it out when you need it. Add some colorful annuals along the walk to outline it in a large enough bed that the color/outline can be seen from the street. If it were me, I'd chose red salvia, white petunias and blue ageratum. Low stuff. Then some big spikey colorful plant in the center of the planters, surrounded by showy geraniums and a colorful spiller like sweet potato vine. Then work on spiffing up the driveway and walk as time and money allows. You can still buy some straggly annuals at the big box store this time of year, cut them back, give them a shot of flower fertilizer (not lawn fertilizer) and they will just about have time to bounce back.

@Denita I haven't considered a door with sidelights before and my first reaction to that was that I like having the option to open both doors but I did a quick search and I agree that it would probably look 10x better. Thank you so much for the inspo pics! I was thinking blue siding too but I am a GB Packers fan so I can always get down on the green and gold ;) Thank you all so much for feasible suggestions! @Yardvaark I'll try and get a pic tonight/this weekend. I'm at work right now. If we do the front patio would you go with putting it in the same spot as my original pic drawing or extend it longer/deeper? Retangle round?