the way you go on about your hill. it sounds kinda dangerous. as in a fire truck would not be able to go and down the hill.
do you have enough land around the driveway, were you could get say a dozer in there, and bring in dirt from surrounding area. and get a better longer hill that does not have as a steep incline. along with such a major difference in sudden grade change?
there are some major areas around here on back dirt roads. and you see flat road, then suddenly it just drops off going straight down a hill side. (old strip mining ground)
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it been bothering for a little bit folks been asking about "grade" and/or slope hills are... get you a clear plastic bottle of water. fill it half way full of water. get on a hill and set it down on ground and take picture. there is your slope of how much the water slants in bottle vs edge of bottle.
everyone has a different pucker factor, of how much the squeeze and suck the seat up into there rear, when ya get into some hilly / ugly situations. and maybe you are just chickening out some due to cost of what ever you are hauling and how fragile it is. and/or you needing to keep the entire pallet of stuff strapped to something, so it does not fall over / packaging comes undone.
my goal is not to push you past your limits. but rather... a bad attempt of trying to get more info out of you. maybe pictures or details of slope / grade / angle or your hill/s
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is there a loading / unloading dock area? were a truck could back up. and use a generic pallet lift? no machine all hand operated / pulling / pushing of a cheaper pallet lift / mover on concrete.