From what you're showing us, we could have any idea of the total volume of water that might come in a rain. But the driveway and the layout (slope aimed at house) suggests that it could be considerable. If there is a lot of water in a heavy rain, it doesn't look to me like you have sufficient grading to accommodate it. Given the state of disrepair you speak of, seems like it's the time to start the design process with a clean slate. Honestly though, I do not understand what you are proposing to to with it. (Any sketches/plans you could post?) You must describe the details of what you propose if we are to understand it.

It's a handsome house, but why does the driveway seem to be the size of a parking lot?

Wow I was all over the place with that first post.

I am working on a scale sketch of what I am hoping to accomplish.

Another thing to note is our septic tank is located on the far left of the patio/mulched area and our drain fields run from there toward shed/parking pad to the right.

Driveway looks huge because it is. I think it has to be paved that much because of the drain fields and also for space to turn around instead of backing out of the driveway. The driveway is next to a ravine and can be precarious in the winter.

I am working on a sketch, but in the mean time here are some more pictures and topography maps.

As you can tell by the pictures we have a TON of work to do outside :-/

The septic tank runs from the first large corner flagstone on the top step to the "V" shaped area between asphalt and patio.

A lot of the water drains down here to the left.

This gives some prospective to the slope. The lamp posts will be replaced with something better. (And driveway needs to be repaired as well).

Each line is 2 feet.

We are still not sure if this will be our "forever" house, so right now just a big bandaid fix to address curb appeal.

I sketched up a design thought. My ultimate goal is to create something that flows more naturally with the surrounding, but still brings attention to our entryway. There is a large creek/marsh that flows behind our house, and everything else is basically woods.

My thought scale may be off though.

I am completely overwhelmed going from a flat 22x100' townhouse lot to 3 acres of slopes/wetlands.

red outline is existing flagstone.

Love those above

More existing angles below:

I'm amending my earlier statement where I meant to say we COULDN'T know how much water was going to come off of the drive, instead "we could." It was a typo.

As yourself, Kmpcfp, if you WANT a dry stream bed, or if you're incorporating it because you think it is the solution. If undersized, they can be "cute" in a mini-golf sort of way. If you expect it to look natural, it should be in scale with the surroundings. Keep in mind that those in the example pictures are on relatively flat ground. If the dry stream bed is expected to carry a lot of water and it's on a slope, it's going to require bigger and beefier rocks if they're going to stay in place. Many times these are built undersized by someone who doesn't have experience with arranging things to look natural and they end up looking like a truck dumped some gravel and it hasn't been cleaned up yet. I don't know what you can do, but be careful not to create that type of arrangement. If you don't necessarily want a dry stream bed (or a pile of rocks in the yard) consider that a tough groundcover is capable of keeping the soil from eroding, once it is established.

These comments are predicated on my thinking that I understand your sketch. You can let me know If I've got anything wrong. First, I would consider that the drainage path (orange arrow) should be pushed closer to the drive and further from the house ... in the vicinity of the orange arrow. The high point (H.P. ... which is the high point of the drainage swale) would be in line with access to the door, as it would be the flattest part of the drainage path. (The blue arrows are the general direction of water flow at the front of the house.)

I would expand the paved access to the house to be the full width of the first section of the porch (near the door ... from the door to the first post). Or it's going to look skimpy for your house. Alternatively, it could be the full width of the porch, more or less like it is now.

Where you are reducing paving, I would get rid of the funky, slanted angles that you are proposing for paving edges and connections, and replace them with straight lines and radius curves. Otherwise, the finished project is going to look like it is designed by someone without experience.

Thank you for the input. I drew it to scale, the dry creek bed definitely wouldn't look right, there is not enough space for what I was picturing in my head.

When I was putting in the curve and the "funky slanted angles" I didn't even think about how the curve would affect the stairs. Reason I wanted to fill in at least the first step was to bring the side of the septic tank to grade. Right now the 4 corner flagstones are just sitting on the septic lid and are loose/trip hazard. And they can't be grouted. What if I just raise up a section of the first step (see drawing)? Should I split the difference and move up a smaller section in the 2nd step?

Each square is 2'

Is the planting bed in front of the window sufficient size? If I have the bed come out 3' it leaves a minimum of 5' for that walkway. I could make it a bit bigger and pull the curve by the septic farther out to compensate.

I don't understand the issues and what you're asking about "raising up first step". Maybe you could show the issues in a picture ...?

Artistically and functionally, I liked it better when you had the edges of the steps to deck with uniform offsets. Why did you change to 2 wide and 1 narrow? In terms of using the steps, I think it works better if you pull the edge of upper step toward septic cover in order to add more space to the upper landing and allow for deeper planting cutout.

I don't think there's a need for the planter cutout to be symmetrically oriented with the wall face. It works better for the steps (to deck) if it's offset and you allow more space between planting cutout and edge of upper landing. (Everything is a balancing act.)

I also like it better when the right edge of the paved approach to the house lines up with the right edge of house, instead of with porch edge. There seems to be plenty of paving. A little more landscape space at the front would be nice. Also, I would consider closing off that last section of porch between the two posts (as per picture) with deck rail.

What you drew with the steps was what I was trying to describe. I agree that the uniformity does look better on the steps.

I like what you proposed. It helps immensely to visually see what I am trying to accomplish. Thanks for your help.

You are welcome and best of luck on pulling it all together.

it was helpful that you posted the background info. -- topographic plan, house plan, photos -- and drew the proposed work TO SCALE.