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Hey Frenchy, this sounds like a neat trip.
My advice is try to spend as few dollars on air freighting the bike as possible. Air Canada used to have a crazy deal where you could ship a motorcycle to Europe for $1200 USD. Airline tickets have gone up 40% over the last few months to give you an idea about inflation.
Used motorcycles in the USA are very inexpensive. You could buy a Suzuki DRZ in the states for $2000 US.
Australia is expensive. I would make that a separate trip in a few years and that way you won't feel as time limited when you are there. I'm not sure how much fun riding the outback would be either. If deserts are your thing that might be fun.
You can find a good deal on a used international traveler's bike in Argentina also. There is a very cheap way to get legal paperwork to allow you travel up to Mexico.
Your brand new CRF 250 Rally has a high chance of getting stolen along the trip. I like how you are planning to use a small bike, but I think a 250 cc is too small for an around the world trip. Trust me, there will be times when you just want to make it to where you are going and not have to do 60 km/hr to get there. I think 350-500 cc would be a lot more practical. Have you looked at the 2012-2016 KTM500 exc and the 2019-2022 crf450r? Those could get stolen too.
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