First of all, how much have you actually traveled outside the U.S.?
If you haven't traveled very much ON YOUR OWN (going to ClubMed, or traveling in a tour group full of Americans, or going to Europe with your folks when you were 14, or living on an American military base doesn't count) I would start there.
I myself have traveled extensively in Europe (and since you mentioned Italy specifically, I've traveled through Italy independently 3 times and love it), Central Asia and Asia, and was an expat living in Moscow, Russia for a year. And while I positively ADORE traveling and living abroad, it is NOT as romantic as you might think. You have to be prepared to learn the language, eat the food choices available (which may mean eating in places that would never in a million years pass our restaurant health inspections), and deal with a myriad of inconveniences, by American standards.
Remember, you will not be staying in a 5 star hotel when you go to LIVE in a place. Are you prepared, for example, to shop in several different stores for meat, dairy, and produce, and carry all of this back to your flat via metro, walking up and down stairs? Are you prepared to give up brand named American products and do more cooking from scratch? Are you prepared to walk to a laundrymat or make room for a washer/dryer in a flat that is already half the size, by American standards?
The rest of the world does NOT live as lavishly or as comfortably or as 'super-sized in every way' as we do. They live in smaller houses and flats, drive smaller cars, and have alot less choices on cable. And they are not nearly as into rabid consumerism as we are - they simply do not have the money. And you
really have to be prepared for all this...because if you aren't, the shock will be tremendous.
Additionally, if you think that by moving out of the US, you will get away from government interference or presence in your life, you are sadly mistaken. In some countries, there is a tremendous amount of red tape that involves schlepping from office to office for DAYS, for all sorts of things that are a phone call away for us. And if you are planning to live in most any part of Europe, you are looking at socialized medicine - not a problem for ME...but it could certainly be a problem for someone who claims to want to get AWAY from 'the government fixing everything'. Government waste and corruption in many countries is standard operating procedure - accepted practice. And if you are looking to get away from our crazy politics...then I would certainly NOT recommend going to pretty much any of the counties you listed. I can't imagine that Central American politics are exactly stable...and Italian politics, while
extremely entertaining, might not be everything you'd hoped for:
http://www.msnbc.msn.com/id/31082171/
And as long as we are on the topic of Italy, if you choose Tuscany you have to be prepared for the Italian way of life - something I ADORE, but which many Americans cannot deal with on a long-term basis. Italians are about the WONDROUS JOURNEY OF LIFE - not about WINNING THE GAME, so if you are an American that is into winning the game, you will have a difficult time understanding the mindset. In Italy - if you expect for things to arrive on time, open on time, keep regular hours, or anything like that, you can forget it. Mass transit can be shut down on a dime...with no explanation offered by anyone - and no point in asking when it will come back up - you will only get a shrug and a big smile. Italy is a wonderful country full of the most friendly people (not to mention the best food) on earth...but they do not, as a rule, take life
nearly as seriously as we do. They are never on time, drive like crazy people and park anywhere they like (and I do mean ANYWHERE), and many laws are viewed more as 'helpful suggestions' by the population. "Good service" in an Italian eating establishment means the exact opposite of what it means here - Italian waiters will ASSUME that you are in no hurry at all and have all afternoon to laze through your lunch - therefore, they will stretch out the service for what can feel like an eternity to us. Eating, to an Italian, is a joy to be savored for as long as possible - not a bodily function that needs to be rushed through so that you can Get Things Done. Italy is a loud, disorganized and wonderfully happy country - to many Americans, it would feel like a country where the party never stops. But you have to be a person who can RELAX and find happiness in utter and complete chaos. It is my favorite country on earth, by a long margin...but it is not for every American.
Finally, I have no idea what you mean by a 'comfortable lifestyle'. But if you expect to find "America....only without that many Americans" anywhere else in the world, you are in for a huge surprise. And going somewhere with that attitude - of expecting all of our comforts and conveniences - will only make you miserable and get you labeled one of those 'ugly Americans' by the locals.
My advise - which I know you won't take since you have never EVER listened to a word I have said on these boards (even about my own profession, which you know nothing about) is to travel - and travel A LOT. Travel
alone and travel like the locals would travel - not like a spoiled American would travel. If you can, take a few months and LIVE someplace and live like the locals live. Walk up 4 flights of stairs while loaded down with groceries that you schlepped through the metro, and see if it's something you wouldn't mind doing. Sample life without all of our conveniences and instant everything. In short, live overseas long enough to really know what you are in for...and if you can deal with your life being VERY different, in terms of creature comforts, than it is here.
Traveling and living as much as you are able like the locals, is the best way of determining if living abroad is for you. KNOW what you are getting into.
But if all of this is coming to your mind, simply because you are sick of American politics and want to escape (which is what it sounds like to me) to a place that is an American Mini-Me without our politics...then living abroad will NOT make you any happier. In fact, for someone like that, it would be an out of the frying pan and into the fire move.