Do you have a brother who has a chick with nice gams? If so, you might be even closer than you think!
I would think it would be MUCH cheaper to employ a personal valet/chauffeur and just go full Lincoln Lawyer. Those times when you absolutely must fly, just go commercial. Fly 1st class with all the money you’ll save not having a copter.
This might be for the cloud thread, but I'm still waiting for a legit hoverboard...not that motorized skateboard crap they use to fool kids who don't know better.
But if you can justify a helicopter for business or tax purposes, live your life. I know in high traffic cities like LA or NYC it can be beneficial timewise or for business promotion at events, but don't know much the cost and maintenace would be to justify it.