Thanks for the response.
Unfortunately, I'm only able to travel during May through August since I'm planning on law school after grad school.
Perhaps I should have been more specific with my questions. I'm more concerned about the climate/weather conditions and their effects on road conditions. I'm not too concerned about political situations, although a lot can change in two years.
I've done long distance riding before. In 2006 I spent 60 days on the road traveling 18,000 miles all over the US and into Alaska (including a trip to Prudhoe Bay). For my next trip I'm pretty much set on riding a KLR.
In general I'm looking for a bit of everything. I'm down for the tourist spots, but prefer to spend my time out in the countryside. I'm definitely interested in some challenges, but I'm also interested in being safe and not reckless (particularly since I'll likely be traveling solo).
When I first began contemplating this trip, I thought about traveling down the Pacific coast in South America to Tierra del Fuego then back north through Brazil. Generally my plan was as follows:
Colombia
Ecuador
Peru
Bolivia (especially the Death Road)
Chile/Argentina
Tierra del Fuego
Argentina
Uruguay
Brazil
Boat ride across the Amazon to Manaus
Venezuela
I originally planned on going during South American summer as I figured it to be the best time to accomplish this trip. Perhaps my assumptions reflect my ignorance on South American travel conditions, so please feel free to disabuse me of any incorrect notions. I'm interested in gathering good information so that I can make proper plans.
Like I said, I'm interested in a challenge, but I'm not interested in being reckless. Some of what I'm interested in:
Andes
Death Road in Bolivia (perhaps this doesn't fit with my requirement of not being reckless, but I don't really care. This is something I definitely want to do)
Atacama Desert
Tierra del Fuego
Rio de Janeiro
Amazon
If this is possible during the time frame I'm able to travel (May - August), then great, if not, then I'll find another trip to do. However, this trip is my first choice.