It seems he had a regular delivery of cats from France to Florida and this was his third trip within a year. In his words
"* I have experienced truly bad conditions out there and discovered how to deal with them – (nice to know should push come to shove again)
* Always, I will go to extreme lengths through planning to avoid bad weather, but on occasions it is karma – being prepared is the key. "
He planned to go via the Azores and was 200 miles NE of Bermuda. It looks to me that he may well have been taking the southern route or largely so, and possibly going via the Bahamas rather than straight to Annapolis. However others will know more of the theoretical and actual route than I do.
In the storm conditions experienced as well as being difficult for any type boat, the cat a 39' would I understand be at risk of being rolled or pitchpoled, so a drogue or sea anchor would be required. That seems the accepted view amongst cat sailors. Whether a new boat on a delivery carried either I don't know.
The two with survival suits survived, the third without sadly did not.