I think you might be over complicating things a touch. Take it one step at a time. Will the house have crawl,basement,slab? Plan where you want the house keep in mind septic (was it perked where you think it might go) you dont want to just decide to move it on a whim like my neighbor and find out the new location wont perk and spend 3-4 times more for an engineered field. After you have an idea where the house and field will go stake it out this will help you visualize it. Get an elevation set (high enough so you can get nice slope away from house in all directions) plan your driveway cut it in and lay down some large stone or crushed concrete and let the delivery trucks do some of the work packing it down (there nothing delivery drivers hate more than bad access or mud) most wont even try if it looks like they will get stuck. You could come to the site and find your lumber package out by the road. The lot dosnt look that bad I would cut a ditch in at the road to fix your immediate drainage problems maybe lay in a culvert and get the driveway base in so you and other trucks can drive back. Just remember water rolls down hill. It can be a little overwhelming at first just take on one step at a time. Dosen't make sense to me to have a bunch of site work performed then dig it up for a basement (just more dirt to move) Then after the foundation is in do some ruff grading hopefully you will have some fill to work with. Oh yea your profile dosn't list any type of equipment. This is prime time to go to the tractor dealer and pickup maybe a kubota M59,L39 or Jd 110 forks,box blade,brush-hog should do nicely for what you got going on you will need it so might as well have it from the get go. After you start construction and the money is flowing the wife will probably bark more. At least thats how it works at my place but my wife is a tight A** you can always tell her how well they hold value and could sell it after the house is done 