Sounds like quite an adventure you have ahead of you! Which country are you starting off in?
[ Edit: Edited on 07-Nov-2010, at 22:57 by bex76 ]
An experience traveler is those already know what to do in their mind, so, that shall be the best palning after all, go with the flow.
Hey ice, welcome back!
Are you just planning to go till the money runs out, or are you hoping to score a paid gig down there? If the latter, I'd try and focus on getting to those countries where you have the most likelihood of getting aforementioned paid gig, hehe. Do you speak either Spanish or Portugese? Have to imagine that will help drive decisions!
which part of SA are you going to? if you are an english native speaker you could get a job teaching at english institutes
good luck on your trip
Assuming you're happy to get your hands dirty, if I were in your situation, I'd head to the wwoof site , find a farm looks like fun and is willing to take me and start the trip there.
Not sure how much Spanish you speak, but immersing yourself like that would certainly help the language skills and provide you some time to think about your next step!