Advice: don't do it. If you're just thinking about it, you don't have the skills to do it at this time. It's not a game, it is very difficult and very dangerous.
Consider yourself a migrant for a bit; travel by the season north and south. Work on your trade skills, sales skills, and barter skills. Learn how to travel with little, yet be effective when you arrive. Keep $1000.
Gypsy around, always choosing the path less taken, and you'll find a new niche.
There are many people that travel from music festival to music festival all summer long; this is another ticket to an out of the box life that just requires some networking skills.
The wilderness ceases to be the wilderness when you set up refuge from the elements.