We remodeled a 1957 ranch a few years ago and had a similar problem. In our case it was the dining room that was at the center of our floorplan and had no natural light. You didn't say what your roof looks like, but in our case we were able to redesign our hipped roof so that we had a gable-end with a window opening to the south right over the old dining room. It's kind of like a skylight, but with less leakage potential. We opened up a portion of the ceiling to make a tunnel of light, and kept the rest of the ceiling at 9'. It really changed the way our house functions. One of the reasons we were able to do this is we remodeled after a fire which destroyed about 1/2 of our roof. So that was an opportunity we grabbed with both hands. We made the old dining room into a study and put a transom window on the wall between the new study and new DR. It works really well to brighten the whole middle of the house.

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.

I would paint the garage doors some color whose intensity mirrors the brick. I don't know what color because I can't see the roof color, which should also be taken into account. You could also paint your storm door the color of the front door to make both stand out.

I would start with the stone first? Replace with brick? Replace with siding? Paint?