Remember, the easy route is not always the best route. I left a job in St. Croix in the USVI, to return to the states and fly passenger and cargo charter in a CE-208 and PC-12, because the IFR time, single pilot PIC Turbine, and more applicable experience was a better step. I miss the Caribbean, but the career step is important.
If I were you, I would CFI until I had part-135 mins, and then try to get on with a cargo operator to build time as soon as possible. The TYPE of flying, the EXPERIENCE you will get, and the VARIETY of situations and decision making skills you will build are paramount.
One of the top check airmen at SWA is a great friend of mine, and I took the Part-135 job back in the states and left the Caribbean because he agreed.
Just my ten cents, good luck!