"If someone has recommended doing half the driveway only and not urged us to do the whole thing, is that another red flag?" In my mind, it's a red flag. Look at the flat cross-section profile of the front portion of the drive. Imagine the heaviest rainstorm you can--one that goes on for hours with a heavy downpour. As flow piles up, it's impossible that water will not infiltrate the building ... unless the entire cross-section slopes away from the building. But it doesn't. Pls8xx makes the point that contractors often propose that which is the easiest/most profitable. Unless their work is very well known to the client, that places their recommendations into question. I'm not saying that the recommendations are automatically not good ... just that they must be looked at with a suspicious eye. The recommendations of a landscape architect WHO IS ALSO A CONTRACTOR must be looked at in the same regard. And JUST because a person is an LA does not mean they are well qualified in all aspects of that work. (I was trained to design a highway, but I couldn't design one to save my life!) ... or that they don't have a profit motive ... or even a lazy streak. Astphard, as I mentioned your property is similar to one I once owned. So similar in fact that it's eery ... not just the narrow drive at the left, but even the paint and trim colors! We had a garage that was too small to be a real garage in the same position. We had a slope (a MUCH more substantial one!) coming straight at the back of the house. There was an existing concrete patio at the back of the house and fortunately, it was swaled and sloped to carry water toward the drive. I swaled the drive to allow the flow to continue. That everyone who has come out to look at the situation has advised installing a drain and piping makes me the lone dissenter. In spite of that fact, I cannot stress enough how much more trouble-free drainage at the surface of the ground is compared to that which is buried. Though I haven't seen a close-enough view of the back of the house yet to render an opinion, my gut reaction remains the same as it was earlier: this can probably be handled with surface grading and drainage for a much more trouble-free, long term solution. Especially, if you're going to be re-grading anyway. Marcinde, you'll see that nowhere am I advising the OP NOT to get a local solution. I'm only advising him on what he should be looking out for while doing it. As well, I agree with pls8xx ... if the proper information could be gathered, there's no reason a drainage/grading solution couldn't be done from afar. But no one here has offered to do one. What's happening here is helping someone to look out for their self.

Be honest with yourself, you're dealing with a problem that is at least 35+ years old and nobody ever did anything. I do believe you're on the right track. Google search on footer drains, and check out Youtube. I highly doubt you will get detailed step by step instructions on GW for this subject matter. Good luck

I use paths like this in many of my designs......they work very well in the wetter weather we can experience here :-) I would recommend using a rigid edging material to confine the rocks - without it, they will mysteriously manage to migrate throughout the garden! And laying hardscaping is one of th few times I DO recommend using a landscape fabric and is a practice my contractor favors as well. It will help to prevent the rock from becoming permanently embedded into the soil (should you chose to move/remove the path at some point) and it also will help to deter any weedy growth that may be lurking in the ground. I would go with the 1/4" minus for the base but favor a larger rock for the topping. 1/4" minus will compact very firmly, almost like decomposed granite, and in doing so will limit permeability - you can develop puddling. The larger topping (suggest 5/8") will provide a better draining surface.

While the standard trench drain is straight, there is at least one company that makes custom curved channel drains. Hope that helps. I do think drainage catch basins would work. They seem to come in 12" or 9" square sizes.