Systems developing off of the tail of frontal boundaries in those locations are not unusual. Further, given the predominant east coast trough and flow that systems would take ahead of fronts, any system developing in the NW Caribbean could likely be drawn to the north and northeast, with tracks like Irene in 1999 and Wilma 2005 across Florida.
If shear remains high, development as we move through the next 8 weeks is less likely. If shear does lessen, even for a short time, and there is a disturbance in this area at the time, there is reason for concern regarding the potential strength such a system could attain. The NW Caribbean is no stranger to major hurricanes even in October....take Mitch and Wilma as extreme examples of that.
Add to this that the TCHP (depth of warm water) is much higher both in amount and surface area right now than it has been in the past 2 years on this date. The fetch of high TCHP extends from the Yucatan to Jamaica to south of Cuba, and even reaches toward the FL Keys and the SE coast of Florida. Compare current readings to readings in 2007 & 2008. This area is essentially an area of 'high octane' fuel for any system that traverses it. Rapid intensification is absolutley a possibility provided atmospheric conditions are even marginally conducive for development.
Current TCHP (9/5/09):

TCHP 9/5/08:

TCHP 9/5/07:
