Nice video. Took me back to my trips down island. Particularly enjoyed the shots of Deshaies and Isles des Saintes to the soundtrack of Southern Cross, a song that means a lot to me. I'm guessing you may see the trip described in the song in your future

The problems with the halyard are pretty common on charter boats. The riggers just pick up the first block that comes to hand without checking if they have a swivel. If they swivel then once that halyards been round the winch a few hundred times it is guaranteed to be a mess, just like yours.