I try with some answers...
Adam,
first of all: Congrats to your decision, it will be fun.
Now some answers:
Contact the local Community in California, I am sure they can help you with the answers concering the import / export / paperwork.
Next, I avoided a US number plate in order not to get all those "special taxes" the Gringos had to pay. Yes, they are treated a little different on the way South... So your choice.
Then for the Middle and Latin Americas I travelled with the Footprint books. Good on details, easy to locate inexpensive alternatives, safety etc. Have a look.
I would ride as light as you can with expensive materials such as laptops and GPS. Why? Well, you will find in every little house an internet cafe with good equipment and uploading facilities for your photos. I did it that way and did not need to worry about my expensive stuff... Secondly, any more chargers and electronic you will put on a bike will increase the chance of a defect.
On clothing, well, you will hit the tropical rains in Middle America as well as maybe minus 10 Celcius in the upper Bolivian Andies.
Japanese light bikes are a good choice as there are everywhere repair and part possibilities.
What more? Take your time, enjoy and listen to the locals...
Cheers
Rasmus
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