FAA has no requirement for this trip, you would not be entering MNPS airspace with a van. No CAA will ask about your previous experience on a North Atlantic route. As posted earlier, this is an insurance requirement, and they will most likely want more than one previous crossing to cover you.
Depending on country of aircraft registry, it might be easier to tank it and route via Cape Verde.
Either way, this is an easy trip. Slow, but easy.
