UPDATE:
I did it!
I bought that one-way ticket to the Philippines, leaving this January!
I decided I'm going to break free from the trap of overplanning and dreaming about something vs. just going for it.
Roosh recently wrote a great article Comfort Will Not Give You Meaning In Life. After reading this, as well as much of your advice, I realized I'm being controlled by the pursuit of meaningless comfort. I'm obsessing about earning great money online, so I can seamlessly go from living and earning here, to living and earning in paradise. No more.
I don't care if I struggle financially for months, or years pursuing it. My basic needs will be getting met, and I will enjoy the process. If I fail and have to come back, What did I really lose?
Anyways, Thanks everyone for the advice. I hope this helps inspire some of the many young men who feel they are in the same boat.