[svnt]

Billionaires typically keep pilots on staff and pay them full-time. These pilots only work for the wealthy or maybe corporate clients and have a nice ratio. Maintenance crews I‘m speculating but in these sorts of situations there are usually a select few companies who are known in that world.

[nicenewtemp84]

Pilots yes, but when you travel nationwide or international, your local helicopter can't make it. So other than your main office location and home, you're probably just chartering a pilot and helicopter. Statistically I'm sure it's ok, but my gut says I wouldn't do it. I also don't let my friends drive if we're going anywhere either.

[lostcolony]

I feel like San Francisco, and in general, the Bay area, is the sort of place a billionaire could rationalize maintaining a crew.