with a 2 am departure crew should be adequately rested and, more importantly, mentally prepared to go flying in the middle of the night.
Absolutely correct, but i know Geoff was making the majority of his cloud 9 business with the transfers to private islands (principally with one unknown client, its client friends and contractors). I can honestly assume that he had been flying the route to the Bahamas several hundreds of times, in a wide variety of conditions. in that context its easy to get more and more complacent with the risks and yield to more and more undo able missions.
Pardon my question: but how do your clear custom at 3am at F45?, would you even have to clear custom while flying VFR without a flight plan?