Scott,
The decision to stop or not in Bermuda is up to you. Yes, the progress of the trip can be a deciding factor, as can impending weather. Hopefully, you will be monitoring weather along the way.
In a CD30, your trip from NC to the VI will be a bit long anyway (say, 13-16 days or so), so the stop in Bermuda would be a pleasant break. Also, Bermuda is a great place to hang out and wait for weather
Bill