Good topic.
I've always dreamed of trying to drive from here to the Tierra Del Fuego....though I don't think that there is a route to do this.
We'd probably want a Chevy Suburban, with a body that looked like it was worn out pretty good (so as not to draw too much attention). We'd have to get reinforced suspension and tires, and if money were not object we'd get bullet proofing done on it.
We'd need someone in our group who spoke Spanish. We'd also need a ninja. Probably KK could do both, not sure.
We'd have to document it all with video, etc. Probably though, we'd just spend most of our time reviewing the beer/tequila/pork products in each jerkwater barrio we ran into.