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So, I've done this, and many people have with the help of Alex at Overland Title transfer service. Look him up on Google or Facebook.
So the bike I bought in Santiago was a Florida plated klr650. Before I'd even arrived in Santiago Alex had sent the new plates (Washington) and registration in my name to the hostel I would be staying at (I'm British and I've never even visited the US).
Once in Chile with the bike and the seller we went together to a notary to make a Carta Poder (power of attorney) document for me to leave chile on the original plates. I left Chile with the Poder and original plates, at the border I switched to my new plates in my name and entered Bolivia on new plates.
PS the border guards both sides were absolutely fine about this, I explained that I'd bought the bike (like every foreigner has, why bother trying to lie to them).
And I left the TVIP in in Chile in the sellers name, I already had power of attorney so couldn't see the point in doubling up on papers. Was no problem, I even went back to the Chilean side to make sure they'd definitely done it.
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