Nice land. How often will you need to traverse that hill? Or other ones like it? Regular winching gets old fast especially as part of a regular path. If it's part of a regular trail, I'd be inclined to cut/fill/regrade that it can be safely done without the winch. If winching is your plan, remember that you could get any vehicle up there hanging off a cable...even a Civic
We will be going up and down multiple times a day. The house is at the top and there is a lake at the bottom. Figured that utility vehicle + power beyond + hyd winch = cable car
The land can be re-graded some, but the soil is nearly pure sand so errosion will be an issue.