If the dude could afford a civvie helo license and then the cost to rent a helicopter, plus his own little island, I think the hotties are attracted to something other than his flight skills. I'm thinking it was little green pieces of paper that are about 6"x2.5", which he probably had tons of.
The island was just public land, and the dude bussed tables at a bar in town......maybe he had family money, but the guy drove a beat up old Honda so not so sure. Maybe he was getting the girls to split the bill on the helo or something, I never looked.