That doesnt have much todo with it in elevation.....I mean,,,2,000-9,000 tops are no different... With Hispaniola,,usually systems travel from E-W across it..while Cuba its S-N only taking a few hours to cross. So that is why Hispaniola destroys more systems plus more waves come across from that direction.
Elevation (yes) does have a impact,,but once the landmass becomes more the flat,,,then any hilly terrain will deminish the straight windflow......another example is being on water compared to a forest or just normal terrain,,,,there is no resistance on water to stop the flow.

BTW you said your a met ? Or did I miss read that? Where you get your degree if you did?