Hi Jon,
I suspect that you will find it more than a little difficult to find an XR. When we tried to buy an XR250 3 years ago there weren't any. Plus, most of the older bikes don't have legal plates, so you can't cross borders with them. We ended up buying a new KLX250, which turned out an excellent bike.
To legally register a bike you need a non-immigrant visa and an address. The address needs to be official with documents, so you can't make one up. You will also need somebody who speaks Thai to get you through the bureaucratic jungle. Don't hand over money until you have the Green Book with your name on it in your hand. You will also need to obtain an official translation of this document from the rego office, as nobody can read the GC.
Carnet shouldn't be a problem, check out the Malaysian AA on the carnet page on HU.
I think you can forget Burma and shipping from Phuket. Either fly your bike from Bkk to Ktm or Dhaca or ship/fly from KL.
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