Cant provide information on all that you seek above but I know in a report earlier this year their pilot numbers were at 171 (excluding) Air Jamaica. Also Earlier this year they had hiring taking place, but required you to be Jamaican or Trinidadian national for Air Jamaica and Caribbean Airlines respectively. From what I know it would be a hard task for you to get in unless you know someone because right here in Trinidad & Tobago there are pilots who want jobs and further more pilots in the Caribbean.
I'm sure we'd see opening between late 2011 and 2012 as the ATRs are expected to arrive then. As its expected that they but the prop pilots into the 738s.
Sure someone else would give you much more insight on this forum.