I keep reading stories of people who do things like this, on HN and I always wonder that how is it that people are able to afford something like this. Do you mind telling us (me?) how you're going to finance yourself for the next 5 years (I think you said you plan to work - freelance?), what you think you'd do once the 5 years are over (if you come back to the US/wherever, do you think you'd still have what it takes to be employed at a similar job again), how you plan to handle the potential loneliness (travelling alone for a long period of time can get lonesome, after a while) etc.?

BTW, having lived in Malaysia and visited some SE Asian countries, I highly recommend it (KL, Langkawi), Singapore and Thailand; but then again, these places were probably on your list already.