I'm considering this right now as a matter of fact. Finishing up my TESL (teaching English as a second language) cetification... which means I probably *could* get a work permit just about anywhere. I would like to move around a lot and travel different places, but right now I am considering all of the following.
Japan: I've always respected certain aspects of their culture and never had the chance to visit before. Shy as I usually am, I think I'd fit in more here, or maybe even have a social advantage for a change in spite of the fact I speak very little Japanese. I know English tutors can make very good money here. I love fresh sushi. Asian massage parlors are fun. I have mad karaoke skillz. Japanese girls are hot.
Korea: Similar culture and money-making opportunities as in Japan. Though I hear South Korea is even more Western than Japan is. My cousin Brett is living here teaching English like I want to so I could have family there. Korean girls are hot.
Spain: I've never been. I actually speak some Spanish. Pleasant weather around the Mediterranean. Daverock has offered to let me stay with him in the Canaries. European girls are hot.
Romania: Not going to get rich here but the cost of living is extremely low. Among the lowest in Eastern Europe. I've travelled through Eastern Europe before and really loved it there. The people there still like Americans. Freer attitudes about sexuality. Nice nude beaches on the Black Sea. Cool places to party in Bucharest. Romanian women are hot. God are they hot...
Poland: Also in Eastern Europe. Low cost of living still though this is probably the most affluent country in the former Soviet bloc. Very laid back. People are extremely friendly. Good vodka. Great food. Good ice cream. Polish girls are beautiful.
Czech Republic: Also in Eastern Europe. Prague is beautiful and fun. Lots of American and British ex-pats there teaching English so they're used to that, plenty of opportunities as well. Lots of good porn shot here. Czech girls are extremely hot.
Hungary: Also in Eastern Europe. Budapest is similarly beautiful to Prague. Great roads... I got the Viper up to 175 mph on the M3 easy. Hungarian women are hot.
Slovakia: Not as many westerners here, so I'd stand out more. I like standing out. Also in Eastern Europe, so good for many of the above reasons. Slovak girls are hot.
Sweden: I've heard many good things. Supposedly very liberal and open culture. Plus there's someone there I've got a crush on. Of course, she's hot. Only problem being I think it may be too dark and cold for my tastes.
Germany: Fun country to hang out in. Berlin is great. The autobahn is awesome, I love driving there. Good food. German girls are cute.
The Netherlands: Among the freest countries in the world, which I love. Amsterdam is great. I like the whole "live and let live" philosophy. Beautiful city, even in the shitty parts of town. Cool red light district. People there are extremely friendly toward foreigners. Very international, like my home town, which I like. Fairly affluent culture typical of western Europe, cost of living is high but moneymaking opportunities are also pretty good.
El Salvador: I speak Spanish. Low cost of living. Warm weather. Spicy food. Salvadorian girls are hot.
Brazil: Portuguese pretty close to Spanish. Nice weather. Nice beaches. Among the most cosmopolitan of Latin American countries. Brazilian girls are hot.
Thailand, The Phillipines, Vietnam, Greece, Italy, France, Russia, China... all other places I'm considering.
Japan and Korea probably at the top of the list right now, mostly because I think I can make more money there than other places and I need to get out of debt.