Horizons Unlimited - The HUBB - From Canada going to SA

Well the title sais it all.

My names nick d cook, im from Western canada and i just started saving for my motorcycle trip through south America.
My parents infected my brother, sister and my self with the travel bug at a very early age and thanks to that i have already been through Auz, NZ, Fiji, Mexico (4 times), a bit of China, thailand, cambodia, loas.... And since returning from south America where I was unable to start my first bike adventure though Vietnam i want to do south America (its all i think about, other then women =p

So i say I'm fairly well traveled for being 25 and a half, don't forget that half! I no longer wish to do long trips alone so this will be my most challenging trip yet.

I have grew up on 600acres of land so I'm quite mechanical, i still have my two xr100's from 1999 and they run like tops.

I have already learned a bit on this site and now my biggest taste is to find out how to go about buying a bike in the shortest amount of time (when I'm ready) and having the least amount of problems with boarders and police. I don't care where in south America i start, I just want the ability to buy one bike and ride it though all the country's. I hear chili is easiest for legally buying but I'm unsure if your allowed to go anywhere you please after, so maybe I should do things the south American way and just buy it from another traveler in cash and make my own paperwork with some cash in pocket for the times a cop does give me a hassle. Well time to keep reading