I just paint out the whole house, except i run my sides long so if/when i mess up my paint marks i still have some offsets to go off of. sounds like you're going to want to start at the top and work down. I situate the machine so that the inside of the inside track is right on my paint line and take a full bucket width outside the line. If i were digging i would probably start off by digging a trench at grade, starting from the top and working down one side so i have a clean cut along that side, and i know where grade is when i start hogging material. I would just throw the spoils from that to that side, it should be enough to backfill, unless you are changing from the original grade. Then i would go back up top and make my first pass across the front, throwing some material up top to backfill and the rest down below. then i would hop down onto the spoil pile from my first pass and do it again. repeat untill you cut the downhill side. Always keep yourself as level as possible, front to back and side to side.
One thing i do is as i get close to the end of one pass i stop ~5 feet short of the side wall and move onto the next pass. i cut out that ~5 feet at the end of the next pass so i have a nice straight vertical wall on all sides. Here is a rough picture if i dont make sense.
Thats hoe do it anyways, always worked well for me. Give yourself two days for your first time.