I think Kobe enjoyed traveling by helicopter as much as possible.

I used to fly many sports team charters over the years. I recall doing a few Lakers charters and coming in late at night to LA and dropping the team off. On the ramp area next to our plane, most of the players had parked their vehicles when they arrived the day before. From the cockpit, we would watch them climb into their Escalades, Land Rovers, sports cars, etc to go back home, but Kobe always had a helicopter waiting for him.

Like the OP, I think this helicopter pilot put too much pressure on himself and over estimated his skills. Trying to ‘impress’ his customers and his employer, got him into a hole in which there was no way out.