Caribbean is a bit different with position reports. Usually when changing FIRs they request that you make the position report 5 miles before the point, so that they can change you over to the next frequency.
Usually went something like this:
You ........ centre, position
Them ........ go ahead
You....... is 5 miles to the Sth (etc) of ....... this time, level at 350, next is ........ eta at 0015
They often readback or just change you to the next frequency. When it is quiet and in the same FIR they often tell you to report when 5 miles short of leaving that countries airspace.
The Jamaican controllers will always want a dme and radial from the airfield when you are within about 120 miles.
Each place has its own idiosyncrasies that you will get used to. Half the fun is trying to understand them some of the time!!
nz