Living in another country is way, way different from going on a vacation in another country. You're removed from the tourist infrastructure that caters to foreigners and you've got to deal with all of the country's bureaucratic procedures and regulations (even simple things like renting an apartment vary ridiculously from country to country). The same places that are fascinating and fun for foreigners to visit are often stressful and annoying for foreigners to live in. Not speaking the native language makes this all the more stressful and bringing people with you that speak your language makes it a lot less likely you'll learn the native language well.

I'm not saying it can't be done, but there's a reason packing off to a completely different country and successfully 'going native' is usually done by single people right out of college who haven't yet experienced a lot of success in their own country. Yes, plenty of older, more-established people do migrate for economic or political reasons, but they usually end up living in ethnic and linguistic enclaves.

My advice? Pick another country that uses English as their primary language, so you don't have that stress going for you, and pick one that's economically developed, so you don't have that stress going for you. You'll still have to adapt to the local bureaucracy, but at least you'll have a fighting chance to understand it. Many English-speaking countries use a points-based system for immigration that favors skilled workers, so you'll also have a much better chance of getting permanent residency.