First let me say that leaving the US is something to think about. The first time I left was in 1975 and didn't return until 1980. However I left again and have only been back for a visit once. My home is in Asia now with no desire to ever return to the US. The life I have here is far better than I could have there plus it costs less.

If you want to teach English its an easy job and pays well. Southern China is better than Northern China and with higher pay. With a TESL certificate Thailand is open. You can also look at SE Asia as well.

You can fly into Hong Kong with a US passport and receive an automatic 90 day visa at no. charge. Obtaining a China visa is easy and only takes one day. I know this from personal experence. My wife and I have lived in China for 7 years. Feel free to U2U me if you want.

When you do decide on a country, join a social networking site for backpackers before you go. Make some connections, network, make some friends at your destination before you leave. This will help with accommodation and maybe even an off the record job (fruit picking/labouring) that doesn't require papers.

Good luck!