The convenience of owning your own helicopter cannot be understated.
It is quicker and safer than taking a car, and thanks to helipads on top of most buildings, you end with better parking spots as well.
The only downside to a helicopter is relying on a pilot to get you where you are going. It makes traveling in a hurry a little difficult, and if you are one that enjoys a private lifestyle, having one more person that knows exactly where you are and who you are traveling with can be frustrating. So dump the hired hand, and learn to fly yourself.
If you wanted to take a lovely lady on a weekend trip to a small island, why do you want to have to depend on someone else to ferry you around? Plus having your pilot’s license is one more little notch in your belt of abilities, and it makes you more self-sufficient. Seriously, what is more impressive and interesting than a man who owns his own helicopter? The man who can fly his own helicopter.
Also, if you have ever had your pilot get sick, trying to find a backup in a hurry is much more difficult than it needs to be. Plus you likely don’t have much of a relationship or sense of trust for the new person who is taking your life into their hands.
It does take a bit of time and effort, but in my mind the rewards outweigh the costs.