Now, granted there's no way I'd ever participate in this contest--I'm too lazy and I'd miss my Starbucks. But, if I WERE to participate, this is what I'd do:
(you need to enlist the help of a partner. Promise him half of your prize if you win.)
Step 1:
Have someone drop me off in the middle of some woods with nothing but light clothes, a map, a compass and some coordinates. (and a camera to document the misery, of course.) Ideally this would be a rather large section of woods that you are completely unfamiliar with. The coordinates would indicate where a small stash of gear would be--a knife, a fire starter, and some more coordinates.
Step 2:
Find the stash (or suffer miserably). If you find the stash, the coordinates indicate some other stuff hidden. Maybe a bottle of water or a jacket. Something to make your life a little better. And more coordinates.
Step 3:
Repeat as long as you have time (a long weekend or a week.) The last coordinates have a cellphone and you can call someone to pick you up. Assuming you hit all the points.
Anyone can feel free to rip off my idea. I won't be using it. I'll be on my leather couch, drinking vanilla coke, watching Bear Grylls and waiting for Schwan's to deliver my groceries.
Good luck, all.