Your house is nice looking. It does need better landscaping. More on that later. As viewed from the street your roof is prominent. That means you can't go cheap on roofing. What you have now is not attractive. I don't know how many more years it will last but when it needs replaced I suggest architectural shingles in a darker shade.It will make a big difference. At that time you could replace the gutters on the front. They just don't look right. If you think you might make changes to the roof line that would be the time to do it. Actually I do not suggest making changes of that sort unless done for a functional reason. It is not a cost with good return on investment. Looking at your stoop I have to wonder how risky it is to change the bulb in the outdoor light. It needs to be wider as mentioned above. A path to the door would be very appealing. It looks like you live in a semi rural area with no sidewalks. How often would the path be used? You will have to decide if it is worth spending the money. I would make an enlarged stoop a priority over the path. What you have now is small enough to look ridiculous. It looks like you have some nice plants. They are not placed well and are possibly too close the the house. Relocate them spacing as suggested by Yardvaark earlier. Perennials will help the bed look more filled in while the shrubs take the time to grow. Some conifers grow slowly. Don't plant shrubs in front of the stoop or next to the steps. Shrubs need room to grow and you don't want them crowding the entrance. It would be worth investigating the cost of a retaining wall on the left side so the lawn could be more level. In the example above I am picturing the top terrace as being your lawn. Here is another area with a patio on the higher tier and lawn in the lower tier. You would have real steps instead of the silly bits of lawn. ^last one You might want to remove the lawn from the area nearest the road. It looks dangerous to mow and would be more attractive with ground cover which can include prostrate shrubs. Here is an image I borrowed from another site. It looks to me as if you could get a wider door and have a solid window to the left of it as opposed to a prefab sidelight. In doing so the door is much closer to being centered. What you have now is nice in my opinion and suits the house. I only suggest if it really bothers you that the gable is not centered. I am not a skilled artist so my mock up is very basic. I see that I did not make the stoop wide enough. It should extend equally from center and I know a handrail is needed too. If no one else mentioned it, a larger light fixture would be a big improvement. It looks like you just have an exposed bulb right now. On the right side I have two recommendations. First that you plant a tree that will stay smallish about 15 feet off the corner of the house. I would also suggest a row of broad leaf evergreens to eventually screen the view of the neighbor on that side.They came out looking columnar which I am not suggesting. Choose any shape you like. Do not add dormers. Do not paint the brick. Do not watch Fixer Upper.

I’m not an absolutist curmudgeon against all remodeling. Do No Harm isn’t applicable to the 00’s McMansion. Or some of the 70’s tract ranches. All of the harm inflicted on those was done in the beginning, and they have no place to go but up. But you just know that some Philistine somewhere sees Falling Water as just some pile of leaky concrete and stone and would propose bulldozing it in favor of a Mini Mart and 24 hour bait shop. Not every home needs to be preserved. Just the well designed ones. This is a well designed home. So much so that any changes should be approached only by ensuring that they are in harmony with the original intent of the design. It’s physically painful to think of anyone putting up shiplap and painting any of it gray. 10 minutes fads are usually bad ones. Wait 5 years If its good design, it will still be good design. If it’s bad design, you’ll wonder what you were thinking.

If the rot isn't extensive, you can replace the rotted boards. If it is extensive, then you might have rot in the structural parts and vinyl siding will just hide it. My house is about 100 years old, shingle-style. The shingles and the porch boards clearly have bits from different eras (with the porch boards, you can tell if you inspect the nails, with the shingles, it's the same thing, you have to be looking very closely). With paint covering everything, none of it is obvious (unless, of course, you're carefully examining the house for signs of older or newer parts) I think wood just looks so much better.

Love the all monochromatic paint scheme. The color to add to your mix to sample is black fox by Sherman Williams. That labor and materials price doesn’t sound that shocking to me I suspect you’ll spend a ton more ripping all that off and putting on hardy and repainting. That said I think Hardy is a good option for you but don’t expect savings