What is your TT?
I dunno what`s with Canadians and wanting to work in the Caribbean, the kind of jobs you posted are not jobs anybody would move far to do, and for sure they don`t pay rent in the Caribbean. There is many young locals with a fresh CPL that are out hunting the few low timer jobs, I have not seen much Skydiving or Glider towing, there are small banner towing outfits and local flying clubs do tours.
If you are able to network with some of the Canadians already working down there you may be able to land a job as charter pilot.