Buy a motorcycle with papers and license plate of the country you are heading to.
 

Hi guys,

Just want to share this short conclusion for those who are not experienced as I was 10 months ago and are thinking about doing big motorcycle trip. When I was coming here to South America I have choosen to go to Chile to buy motorcycle, mostly due to good time to visit patagonia first.

At that time I thought that the best and obvious thing is to come to the country and buy motorcycle from this country where you are currently. Because of paperwork, security etc. But now I know it was wrong approach.

So If you coming to Chile and want to go all the way north, buy motorcycle with Colombian/Ecuador papers and plates. NOT CHILEAN! Will make your life way easier, what's more, you will probably buy this bike in very good price in Chile and sell in even better in Colombia. If you do opposite, as me(idiot), You will pay a lot in Chile and then sell for half in Colombia.

Of course always check all documents, title transfer and border passing issues etc. But save your money bro!

Probably for many its obvious but maybe at least for one person no. For me wasn't.

Cheers!

What you are saying makes sense, but my advice is not to focus on making a profit on the sale of the bike.

I think you are better off buying the bike cheap to start off with in Argentina/ Chile from a foreign traveler and than just selling it for $1000 in Colombia for a quick sale.

When buying the bike you should focus more on the quality and price of the bike, than the home country. You could wait 6 months before you found the right used model from the home country you are shooting for.

You can waste a lot of time and money trying to get that extra thousand or two out of your motorcycle. It is much better to just fire sale it and move on with your plans.

But insurance wise, does it matter what plate is on it? Like, does it matter if I buy a bike in Colombia with a Colombian plate or buy one with a Canadian plate?

I'm planning to drive from Colombia all the way through South America and end in Brazil.

Canadian - or any other bike insurance - isn't valid out of their "region" (Canada / USA have reciprocal agreement on insurance).
You buy insurance either at the border in South/Central America, or before you arrive in North America.