If you choose to go the SE Asia route you might want to check out Yunnan province in China. It's basically between Vietnam and Tibet, apparently has great weather pretty much all year and I found the people there to be pretty laid back and really friendly. Food is good, everything is cheap and there are some pretty cool travel destinations. It will not be as easy to get around as Thailand would be though. It's well set up for tourism, though the tourism is mostly Chinese tourism. Nonetheless, if you're comfortable with adventurous travel it could be somewhere really cool that not everyone has been to.
I may be heading back there in another week and taking my mountain bike to spend some time just riding around in the countryside. I'm also looking at the possibility of moving to the capital city there, Kunming. If I do, I may be able to offer some couch surfing for you and your buddy.
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