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Excellent thoughts. What is the best source for job listings in Puerto Rico? Can I find the kinds of jobs you listed above advertised online in English, or should I get a Spanish speaking friend to help me peruse/decipher Spanish language job ads?
As for the comments above about road quality--- I recently tracked down a high school buddy of mine whose dad's side of the the family lives in PR. He too said he prefers driving in San Juan because unlike other parts of the island it has a "first world infrastructure". I managed to master driving in urban Korea, I'm guessing San Juan wouldn't be any worse, might be easier in a pinch. (Having said that, urban Korean driving is kind of stressful.)
I still lean toward wanting to live in rural PR, but the road quality is indeed an important thing to consider.
All of these questions are somewhat academic for now, as I accepted a public school English teaching job in Louisiana, and will be there for the next year or two. But my wife and I still would love to go to PR after that, or sooner, if Louisiana falls through at the last minute. (Hoping it won't, and I would imagine that public school English experience on the mainland will make it easier for me to find teaching work in PR later.)
I'll watch this thread to see if any more advice comes trickling in. If not, I'm sure i'll be posting more queries in the next 8-20 months.