You will need to convert to the Trinidad and Tobago CPL by doing the conversion exams, passing a medical and if your flying skills are current, you will not need to take any flying test. But this can change according to the T&T CAA. Contact the CAA administration office for more details.
Civil Aviation Authority - Home tel: 868-669-4302
If you were born in the USA, my advice is to stay there. You are a citizen, which means you can get your flight instructor rating and build hours then join a regional, and then a major. Why come and fight up in a small market like Trinidad?
You will have far better opportunities and a broader range of flying in the US than you would in Trinidad.
You really need to know someone down in Trinidad to get your foot in the door! Caribbean Airlines may start hiring soon as they are expanding a little. But besides Caribbean Airlines, there is Briko and the Air guard. But the latter two are more difficult to get into than Caribbean Airlines.
My advice, at your age and with a fresh CPL, stay stateside man!
