Horizons Unlimited - The HUBB - Buy in USA and south or buy in Chile and ride north?

Hi guys.

I am going to be in Brazil for the World Cup in June/July 2014. Sweet.

I have been riding for years but have done no O/S riding before.

I will be in Rio end of June start of July but am looking to travel for another 6-7 weeks on top of that. Not overly fussed which countries I visit but would prefer South America rather than Central.

There are several questions...

1. Should I travel for 6-7 weeks over April/May/June or travel after the world cup in July/August.

2. I want to be able to ride the bike basically anywhere...what is the best country to buy in/have the bike registered in??? I am even happy to fly into the US and ride south through Mexico and Central America...

3. The two options I am considering are fly into southern USA and go south or Santiago and go north...given the time of year which would be better?

4. I REALLY DON'T want to spend weeks waiting around for paperwork to be done, which country will expedite the process most quickly?

5. Is shipping a bike from Australia a viable option?

6. Any countries/areas I should avoid. ie dangerous?

I feel the more I read the more confused I get :confused1:

Ideally I would Like to travel before the world cup and then have a month to sell the bike in Rio while the soccer is on...is this possible from what I can tell selling a bike outside the country you bought it from is problematic?

Sorry I know I am chasing a lot...