It would be fairly easy for you as there are quite a lot of Americans moving here and British also, most cities here have English speaking staff in bars, shops and restaurants so that is not any kind of obstacle, food and drink is superbly cheap with a half litre of beer in most bars costing around $1.20 US.
Why did I pick Poland, well half of the reason is my wife is Polish and that makes it easier for me to be here, I did live in Spain, Malta, Thailand, Hong Kong, Singapore, Tenerife and a few other places before deciding on here, and this seemed to be the freest place there is. There is low to no crime, the schools are excellent, people are friendly and mind their own business for the most part, younger people respect older people like it used to be in the UK. And you get a very nice spring, summer and autumn here.
Anything else you would like to know please feel free to ask. I would suggest maybe trial it, as in take a holiday here, maybe Krakow, Zakopan or Lublin to name a few places.