Hi Danny,
With no pressing time frame for your trip, buying a smaller capacity bike makes a lot of sense, smaller bikes are cheaper to run on a multi year trip. I am a big fan of Yamaha 250's, (TTR, XT, WR) they are great little bikes with engines capable of high miles (AS LONG as they are looked after with regular servicing) they are rugged and easy to work on.
The DR350 is loved by many and is certainly capable, the extra bit of power is good over a 250, but it comes down to how well any used bike is looked after and what work has been done - or needs doing to make it ready for a big trip.
Take these bikes out on a test ride if possible and see which one 'feels' right for you to ride long distance. Look for blue smoke from the exhaust on start up, any rattles or odd noise. Any used bike with more than ~30K miles on it, I would change the clutch on it before I set off on a big trip and a 250-350 with ~50K on it, I would put in a new piston, rings, valve stem seals and new cam chain if it has not been done already. Get familiar and used to working on your bike at home if you are mechanically minded.
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