I have a hard time understanding why anyone would want to be cruising down there during cane season.
Well, if one really enjoys uncrowded anchorages and quiet bays, the only time you are going to get that is in the summer. There are quite a few eastern side anchorages that are completely unavailable at any other time, so cruising in the summer is the only
time to go.
Perhaps, if you had been down here before satellite/internet weather, when you knew a storm was coming more or less toward where you were but only that it was going to strike you directly when it hit the other side of the island, you would consider sailing in the hurricane season today as safe as sailing anywhere. After all, you can hole up in Grenada and an Ivan can still ruin your week.
I think one would have to be pretty inattentive to get hit by a storm in the Windwards or Leewards in these days of satellite/internet weather, as long as you are prepared to move your boat a hundred miles or so north or south. It's always a mistake to get lulled into complacency like Mark did in St. Martin, and then get hit by a "not yet developed" tropical storm, which turns out to be a hurricane.
However, especially after the Dorian fiasco, I think we can all agree that if you have to rely on the weather forecasters, then perhaps cruising the eastern Caribbean in the summer isn't for you.