The first question was: what are the chances of succeeding? Which might be the risks? One very good source of info was ADVRider. Then we used UNESCO World Heritage Sites List to find out what is worth seeing. In order to get to see as many interesting things as possible, we decided to go southbound on the Pacific Coast, until we reach Tierra del Fuego, and then ascend on the Atlantic Coast.  In order to avoid the risky Darien Gap we will have to take the ferry from Colon, Panama to Cartagena, Colombia. There is only one country in our trip that has visa requirement for Romanian citizen. That is Bolivia, but fortunately they have a consulate in Los Angeles. I will get back later with a more detailed plan, once it will be completed.