Hello Guys

As the title tells, I am a guy from Switzerland and I want to go on a trip around the world on a motorbike. I have to work until November before I can start, but then it's winter in Europe and therefore I am planning to start somewhere in Chile. First I wanted to ship my BMW F800 GSA there, but as the shipping is quite expensive and the bike is too heavy for me anyways, I decided to sell it again and now I am thinking about buying a new one directly in Chile.
I saw that there are already many threads about this topic and I read many of them. But here I would like to ask for very specific tips for my own trip.
So my first question would be the following:
1. If I get a chilean licencseplate and insurance, ist it also possible to drive the bike to different continents with that plate?
2. I am thinking of buying something like a crf 250L or DR650 and build it up as adventure bike. Does anyone have a contact of someone with skills and garage to help me buy & build up the bike?
3. Is this whole idea stupid and should I just buy a light bike here with swiss insurance & license and just pay the price for shipping?

Again, the plan right now is to just buy a ticket to Santiago (or similar) and stay there for maybe 3 weeks to learn spanish and organize the whole material for the trip etc.

I would appreciate any kind of help

P.S. I recently made a test trip to the UK on my BMW and I really struggled with some light offroading, therefore the whole Idea of selling and rebuying a light bike came up. If you like you can watch a little video about my trip and my learnings here -> https://www.youtube.com/watch?v=ct1pPNEKXRY