One of the great advantages to PLANNING is that, even without money to do something now, a project can end up being great even when you take 10 years to do it. To be sure, the scene will be dramatically improved by adding a hard surface driveway. If you can use an upgraded material for it, all the better. At minimum, you need to lay it out so that it is attractive and functional. Likewise, create a much larger stoop at the entrance and connect it with the driveway in a way that doesn't rely on a skinny little walk in order to make the connection. Be sure to pull it far enough away from the facade that you allow for decent sized foundation planting spaces. (I've got to say I don't care for Digdoug's walk layout, especially the way it connects to the drive at an angle. I'd much rather see one that tied to the drive at 90* and didn't look like it was heading for the mailbox at the street, especially since you'll mainly be using it to go from house to car and back. If you're going to work out a layout yourself, you could get feedback here, if you post a simple plan. There is not much point in thinking about planting, except in a general, uncommitted way before you commit, to a hardscape layout, as the former is subordinate to the latter. Over the long haul, it would not be that difficult to add a roof covering over the entrance stoop. Doing so would make the house look much more welcoming, as well as giving physical protection to those entering, and it would add architectural interest, "breaking up" the somewhat boring, unadorned, long roof. I like the sound of your "light grey & white trim/black shutters" paint scheme. Be careful not to go too light with the grey (taupe) or it will look bland. Look at paint samples from a distance (like from the street) when appraising them. I would even paint the foundation. It could be the same color, or different from the wall color. If it is block, you might stucco it first. Also, explore the free online paint visualizer programs that allow you to explore different colors on a picture of your own house. Insofar as taking the house in a craftsman style direction, it seems like you would be employing some architectural devices that are seen in craftsmen style homes, such as brackets for the roof overhang. If you add a porch, there would be an opportunity to use craftsman style posts, etc. How successful the transformation ends up being would depend on the details. You might start by drawing a "to scale" elevation of the house and exploring your ideas on copies of it. You would not start by constructing things in order to try them out. Preserving the good ideas and refining them on a drawing would go a long way toward letting you know if they're going to work.

@visualizemaven Thanks for your response, and those photos are gorgeous! Love the earthy/industrial vibes and the stone. We might one day add stone to the bottom half of the exterior right below the midline trim, but it's looking like it's out of our budget for now. All we have planned at the moment is paint/roof/landscape. Metal roofs are very uncommon around here, but I'll look into it. Also appreciate your thoughts on colors; I'll admit that I'm a bit color-challenged. Any ideas on what would be better?

We have a side yard. This satellite image gives you a better idea of the house position. The road to the left of this photo is technically the front of our house, but as you can see, our carport is off of the little alley that ends at our house. That is the only way we can get to our house since the front of the house is a hill.

Thank you, both! I certainly understand and appreciate where you are coming from. Waiting has been our mindset for a long time. We have lived here for ten years mostly focusing on saving, doing infrastructure projects, and tackling smaller landscaping projects (it is on 3+ acres and much has been done in the back). It doesn't look like much now (spring has not really arrived where we are) but the beds will be full with plants soon as it warms and we always plant annuals, planters, pots, and baskets. The greenery always does wonders to make it look more welcoming! We have gone back and forth about waiting. Unfortunately, the paint has been slowly running off the house when it rains since we moved in, some places are down to bare aluminum, and the deck has not been done for three years and is in need of painting anyway. We feel like we need to address it now in order to maintain the house and keep from opening ourselves up to bigger issues down the line. Aside from the painting (which we plan to do ourselves) the other projects should not be impacted when we renovate (patio furniture, trellis, steps, etc.). A good chunk of the funds will go toward furniture and based on our budget estimates. The paint and associated supplies will represent a much smaller portion.