I used to browse this online magazine. http://www.escapeartist.com/ http://www.escapefromamerica.com/ http://www.escapefromamerica.com/category/living_overseas/ Some good articles/tips from ex-pats but be wary of the sponsors flogging international real estate and "asset protection." The good (?) news about Costa Rica is that many have made the move before. Like parts of Mexico and Panama, you can pretty much have an American/Canadian lifestyle if that's what you want, and plenty of people do.
Good question. I hadn't thought of it as so long ago but in fact I was last there in '96. That is a long time ago and it could be quite different today.