If you want to travel through several countries, I think flying your bike out makes a certain amount of sense. There are lots of posts on this forum about buying a bike in a country where you are not resident, and the paperwork involved is usually quite hard - you never know if you have got it right until you hit the border and try to leave.
Buying a bike from another traveller is also a gamble, unless you are British, and can transfer the ownership documents online and make the physical handover at a border (in no mans land so it leaves the country with one owner and enters the next with a new one).
I will happily be corrected by anyone who's done it successfully, and I know it can be done in Peru, but be very wary elsewhere. Plenty of folk will take your dollars and run, leaving you with a bike you can't use or sell.
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