[jimbobob]

I recently went on a backpacking trip with the thought of working from the beach in Thailand in mind. I spent a couple months there, both in the South near Krabi and later in the North (Chiang Mai, Pai).

The good: You can live a pretty good life for quite cheaply. Depending on where you are, I found the Internet connections to be decent, the food to be tasty and the people kind. If you stay there long-term it is important to pick up some of the language as it will bring you closer to the locals. You may also find that you are able to get better prices as a result.

You can do border runs quite easily (Cambodia, Myanmar, or Malaysia). There is an entire industry that has developed around this purpose. When I was there, the visa terms were different depending on if you flew into the country or if you went over a land crossing. I would check out the latest situation on WikiTravel or the Lonely Planet forums.

I personally met another American who over-stayed his visa by over a month. Believe me, you do NOT want to be that guy. He had a horror story about the situation, and ended up having to pay a hefty fine.

Feel free to reach out to me if you want more details.