Hi Duncan,
Congratulations on completing your studies.
The easiest plan is to buy a bike in county A, ride around, visit other countries and go back to country A, then sell the bike.
Whatever country you pick, a it's the same drill, find a bike and getting through the paperwork and buy insurance, in Spanish. There are lots of details in the forum on how to navigate the system in Chile. Some breeze through, others struggle.
It sounds like you are in touch with Toby. I have ridden with him and trust him 100%. He'll take good care of you, set-up the bike (new or used) and get you squared away with paperwork in ~10 days. Research this forum and you'll find names of people that will do the same in Chile. YMMV. I'm buying a bike from Toby this fall and will store the bike with him in between trips. I have a multi year plan...
A few things I have read in this forum over the years or heard from riders that I have met:
- its hard or impossible to buy a bike in Argentina and ride it out of the country (at least for a set amount of time after purchase, perhaps one year?)
- you can always buy a bike in one country and sell it in another country, but there will be important duties owed by the purchaser when registering the bike in the new country
- for some reason you need special paper work when buying a bike in Peru, then entering Bolivia from Peru
There are stories of people selling a bike bought in country A to someone in country B, and the new owner is never going to register the bike. The bike will live out its years within the property lines of a farm...
There are stories of people people selling there bike to another traveler. The paperwork gets confusing, I have no advice on details, but it is done.
Its not uncommon for riders from North America to travel to southern South America and want to unload their bike. These are usually exotic/luxury bikes by South American standards and easier to sell. A $1,700 Sumo could be considered a 'disposable' bike when compared to a $20,000+ BMW 1200GSA. I think you will have a grand time on the Sumo! But chances are you aren't going to too terribly much for it when you sell it.
There are many ways to plan and then there is the reality that rules are sometimes flexible in South America. You'll see. In the end, I recommend a round trip starting in Peru. Know that there is a LOT to see in Peru! You could easily spend your year off riding Peru, Chile, Argentina, Bolivia, then back to Peru...and have an amazing trip!
PS: Assuming you are a US or Canadian citizen (and a few other countries) you'll have to pay a 'reciprocal' fee to enter Bolivia, Argentina, Brazil (visa must be secured BEFORE getting to the border) and Chile(?) Amounts vary, but expect to pay around $130 (USD.)
__________________
Peter B
2008/09 - NJ to Costa Rica and back to NJ
2012/13 - NJ to Northern Argentina, Jamaica, Cuba and back to NJ
2023 - Peru, Brazil, Paraguay, Argentina, Chile, Bolivia...back to Peru.
Blogs:
Peter's Ride