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My opinion, it doesn't cost that much to at least "try" your lifestyle choice before you make any concrete decisions. I tend to err on the side of caution. That's part of the planning process. Save some money, enough to last a year overseas, bail for a bit, and head on over to Asia. Experience things so you can see if it meets your expectations/preconceptions. A year isn't so long that it destroys your marketability in the US IT field.
Last thing you want to do is make a big mistake. I'd say most of us here have tried the traveling thing before making any permanent plans.
I would try different areas(but not limited to), like a 2nd-4th tier Chinese city, different areas of the PH, hell, even Vietnam if you wanted lol. Also consider the quality of perspective mates in the regions you'll be traveling, if that's real important to you. And don't forget that if you do plan to reside permanently, that you will need to learn the language.
Sooooo, if your not happy, save some moolah and move your ass. All your doing is wasting your life away according to what you've stated yourself. Even if it doesn't pan out, these kind of life experiences are really something and they'll stay with you for the rest of your life
Sounds good, thanks guys. Maybe the best thing really is to figure out the online passive-income thing... At this rate It'll be at least several years before I'll be able to give the Phils a shot just working my day job and saving up, so that should be plenty of time to give the online thing a try and get it producing a steady income if it pans out.