As for support, I do have some from my family in case of an emergency, but its certainly not infinite.
I feel like in life, I've consistently taken the safe route. Now, I'm really tempted to take a huge chance.
I know that taking a year or two off to teach English would generally detract from my career, but I also am very self-motivated, and I would probably spend a good amount of that time building my programming skills even more.
tl;dr: Should I take a mid-pay job with high potential for future salary, but be locked into a particular location, or pursue a life-long dream and teach abroad for a low salary with low potential for future salary?