I'm also a West trying to trace ancestors from Montserrat without much success. My grandfather George West was born on the island in the 1890's. He came to New York and married Esther Boatswain, also from Montserrat. Their three children were very young when he died (around 1930), so very little family history was passed along. I know that he had at least one brother, James and that they both worked for a while in the Panama Canal Zone in the early 1900's. He may have had sisters Ellen and Eleanor. I don't know if any family went to Cuba.
Somewhere on the Boatswain family tree, there is Sam Dyer .(I think born in England, possibly in the 1930's or 1940's. It's hard to tell from the info that I have.) So far, that's all that I have. Let me know if you've had any luck in your research. Thanks.