Preparing for my adventure

In October, I am planning a to ride my bicycle from my hometown, Austin, Texas, to not quite the southern tip of Argentina and afterwards to Rio de Janeiro. I will not pass through every country in central and south america but I will pass through many. I rode a shorter ride in the summer of 2001 when I rode down the west coast of the United States. In that trip, I spent $2,000, rode 2,900 miles, and took 2 months to do it. In this trip, I hope to spend no more than $10,000, estimate that I will ride up to 20,000 miles, and take up to a year doing it. When I arrive in Rio de Janeiro, I hope to find work teaching English. I taught English before when I lived in Mexico for a year. I would like to stay in Brazil long enough to effectively learn Portuguese. I do not have definite plans for my return. I have saved up a healthy chunk of cash from waiting tables and living a simple, car-free lifestyle and I, hopefully, do not have to worry about running out of cash flow.
Why am I doing this? I am doing this because life can be tedious and, dare I say, stultifying. I am young, I do not have people who depend on me, and I have managed to escape the impoverishing traps of massive student loans and car ownership. As far as the method of travel that I have chosen goes, I can't think of a way I would rather be going. I am 28 and proud of the fact that I have never driven a car. The bicyle ride to work is almost always one of the most enjoyable parts of my day. I love going on long bicycle rides. I love zooming down hills. I even love riding up hills because I see every hill as a personal challenge to be conquered. Life gives you hills. When one spends a lot of time on a bicycle, bicycling becomes a metaphor for life. One discovers a lot about themselves when they overcome challenges and adversity. I am looking forward to the adventure. I will post more about my planning and preparation later.