I am still toying with the idea of moving to PR. This has brought up certain semi-philosophical observations.
You might approach it in regards to risk/benefit. Just like in the stock-market, greater risk has the potential of reaping greater rewards. The rewards are that you improve yourself, as a person, more or less. The risks are that you will be miserable.
Now, "calculated risk" is a more subtle thought process. The main ideas are to do your homework, and don't burn any bridges.
In doing your homework, I suggest spending many hours contemplating what you would like to experience in PR. Become VERY versed in Puerto Rican geography. Become VERY versed in what you need to do regarding housing, healthcare, education, shopping, and security.
Regarding not burning bridges, perhaps talk to your present employer and enquire whether there might still be a position for you in, say, six months if your experience in Puerto Rico is not what you hoped it would be. Also, have a return ticket in hand. Of course, I have not yet made the leap, so this is purely conjecture. Any additional thoughts, especially regarding how to minimize risk? Lastly, my experience, so far, is that English is not as widely spoken as I was led to believe.