Hiring a "local" Captain I suppose means a Bahamian rather than a US Citizen. That may cause problems with your insurance
company, if you are insured. It also raises problems with "Visas" for the Bahamian which would have to be resolved whereas a U.S. Captain would not have that consideration.
-If - the next good weather window might open mid-February or later, doing the route
in the classical way (Bahamas, T&C, D.R., P.R., Virgins) makes sense. You can utilize the time waiting for that "weather window" exploring the Bahamas and the D.R.
But the whole thing is really a big "crap-shoot" as good weather windows historically come once every 4 or 5 frontal passages off the US southeast coast. So you may wait 2 days between "windows" or 2 to 4 weeks. I suppose it depends upon your good "Karma" with Mother Nature. Point is, if you "have to get there" more than likely Mother Nature will thwart your plans as best she can. Nobody knows. . .
The route is classical - get Bruce VanSant's "Gentleman's Passages South" or "Tricks of the Trades" for important background information on how to do it. Basically, the route is to go from Georgetown, Exumas to Mayaguana and wait for a window to cross to Provo in the Turks & Caicos.
Then move across to Long Cay on the eastern side of the Caicos Banks and wait for another window to head
south (Long Cay to Great Sandy Cay to Luperon) to the D.R.
Then wait in the D.R. either at Luperon or Ocean World, Puerto Plata for a weather window to get to either Samana, D.R. or cross the Mona Passage
to Mayaguez/Boqueron, Puerto Rico.
Then puddle-jump in the early mornings along the south coast of Puerto Rico to the eastern side. Beyond that it is easy.