I was taking a break today and looking at the driveway about where the 710 contour line crosses and was thinking the same thing you mentioned. The ditch on the north side of the road doesn't have any place to empty until it reaches the county road and by that time it could flood my driveway during a good rainstorm. Maybe another option is to cut a small ditch near the top of the hill to direct water over the north side of the hill? It wouldn't have to be very long because the driveway is pretty much on the ridgeline. I made another picture to show what I mean. As for the pipe near the county road I am planning on calling the county Monday to have the road commissioner meet me out there sometime this week to voice my concerns.
I've already purchased the geotextile fabric, so I'm pretty much committed to using it. I did a lot of research before deciding to use it. Most of the negative feedback I found regarding the fabric revolved around the fact that it is expensive. I shopped around and got what I feel was a pretty good price and I figure that I'll never be able to add it later, so it seems worth a try. I'll have to let you know in a year or two if I have trouble. The reason for the 1 inch minus rock with 10-15% fines is because that's what the salesman recommended. He said to use 6-8 inches, but I figure on having 8-10 to be safe. If you guys have other suggestions for aggregate over fabric please let me know.
Hopefully the dirt doesn't compact a bunch because I don't want to have to go back and move a bunch more. I could probably live with an inch per foot, thanks for the suggestion.
Got about another 8 hours in today and had a couple of setbacks. Pretty much working on the top of the hill now and there is a LOT of topsoil. I really struggled with the first section on top of the hill due to the topsoil depth of 12 inches in some places. It seems like I have to move 3 times as much dirt as I should. My wife came out late today and we were looking at the area we have staked out for the house. Of course, we started thinking of some other options and we ended up moving the stakes. Hopefully I haven't gone too far with the driveway yet....
Struggled so much with the topsoil today that I'm going to try a different method for the next section, hence the picture where I started cutting on the sides with grass in the middle.



