If you were that rich wouldn't you just hire someone to drive well for you? But if you liked driving for the sake of it would it not be part of the enjoyment to learn to handle different vehicles well?
I'm sure it varies, but personally I have a very prosaic reason that I would still drive myself in most scenarios: If someone else is driving I tend to get motion sickness.
Expense? Just hiring a car would not be much more expense but would require more logistics, as you would have to manage scheduling and calling cars. To get a dedicated driver, or team of drivers (to cover 24 hours) and vehicle would be significantly more expensive than a couple extra vehicles. Plus handling the logistics of setting them up to be ready and waiting for you each time you travel would be something else to manage, or would be something to pay a personal assistant to manage. Plus you could still use car services as needed whenever you didn’t want to drive.
Unless you had reached a level where you were having almost everything in your life managed by assistants, and you were the type of person that wanted to give up all that control, then have “your car” ready to go whichever house you were at would be the lower mental overhead solution.
As people are discussing there are different level of rich. At some level one want to reasonably good car that they drive themselves. At another level maybe people send advance team to setup before owner reach their vacation mansion and drive them around, cook their meals, etc once they are there.
> maybe people send advance team to setup before owner reach their vacation mansion and drive them around, cook their meals, etc once they are there.
I can readily believe this does happen at the right level of wealth, but there's something deeply absurd and humorous about someone sending a vanguard to their second or third home before they arrive.
I mean the level of conveniences in developed world are already much much higher even for middle class that we don't even think of them as luxury it would be for > 90% of world population.
My very typical American suburban home on a 0.2 acre lot is better built, has better views, parking, heating, cooling and so on than a 3 generation rich (from my standards) cousins' home in India. However they do have half a dozen servants at home and I have obviously none here.
So it does sound weird that people seek even further from developed world middle class point of view.
Most people don't really like it, but find it to be the best option to go from A to B quickly. If you involve other people, be a driver or a renting business, you add complication and cost.