He was doing precisely what he said he liked to do in the interview regarding hurricanes: Getting a good ride out of them....
Well no, he was not doing precisely what he said. He said he "chases hurricanes" and likes to get into in the southeast quadrant. But he wasn't actually doing either. By chasing in the southeast quadrant, I believe that he means he follows the hurricane as it moves to the north, staying in the southeast quadrant where the following winds would push him to the north. In this position, I would think that, if conditions get to be more than he can handle, he can reach off further to the east, and allow the hurricane to move further away from him. In the southeast quadrant he would always have a way out from this.
It appears from the path he followed that he did not attempt to get to the east as he stated he would. And I wonder what he was thinking, because such a position would require him to beat close-hauled to make headway toward the south, which was impossible on that boat. And, of course, he wasn't chasing the hurricane - it was chasing him. He left himself no way out.
So one of the mysteries to me is why he said he would say he was going east of the hurricane on a southerly itinerary, since the breezes east of the hurricane would be pushing almost directly against him.
So beyond simply being a stupid decision to go out, it seems to be self-contradictory that he would say he's heading for the southeast quadrant on a southbound itinerary. It just does not make sense, but I suspect the experts at USCG will cover all these questions and more to get to the true root cause.