I hit the trail in 2000 with right around $400.00 and I never wanted for too much. I lived on and off of the trail for about three years. I worked some and sometimes people insisted on helping me out, I didn't have to beg.
That being said, I plan on hiking again soon and taking tater peelers with me to finance the hike. In fact these peelers just financed my trip back to Kansas and then back home.
So I'm saying that you can do just about whatever you set yourself to do but always remember,you can plan the plan but you can never plan the result........
Just go and hike, and if your a pure person people will notice and help you find work and your most basic needs will be met. Besides it is quite a bit more adventerous to stop and work along the way, plenty have done the entire trail this way.