I currently know three separate family units that are relocating overseas. I mostly follow their progress via their FB accounts.
Two of them are moving to Portugal and one is moving to Belize. The ones that are moving to Portugal are impressed with the ex-pat community there and found it very easy to connect with others as they began the process. One couple is able to work remotely for the U.S. companies they are currently working for here, and the other youngish woman intends to find a job there - she has desirable skills. But both families have fallen in love with Portugal - reasonable costs of living, great health care and again, a strong ex-pat community that is very supportive of new applicants.
The couple moving to Belize is probably close to retirement age, but again, have fallen in love with the country. I don't know if they plan to work remotely or are currently ready to retire.
I do know that all of their stories have included long wait times for application process and getting Visa appts., like many, many months if not a year. In the meantime, they travel to their desired country every few months to take care of needed business. One tip that one friend mentioned about getting her Visa appt. - she had tried for weeks on end to nail an appt. Then someone suggested she change the browser she was using on whatever website scheduled the appts., and she quickly was able to get an appt. 4 1/2 months out. So if you decide to proceed and have a problem getting an appt., try changing your browser.
I guess your only downside of Portugal would be they speak Portuguese, but as sisoon says, most people in Europe have at least a rudimentary grasp of the English language.
Good luck!