This is very interesting, thanks for sharing.
I'm not really seeing the the "spoiling" or pampering part of the experience, though. Fly PIT to LGA, crosstown Uber through midtown Manhattan, then jam into a helicopter bound for HPN just to play footsie for 5.5 hours underneath a shared tray table? What about it was luxurious enough to justify an otherwise unnecessary >4-hour dogleg and less personal space than commercial transcon F?
This seems like a very worthy supplement to commercial premium class travel and a great backup option for frequent coast-to-coast business fliers. But once you remove the itinerary control and the privacy of a chartered flight you're left with a packed aero-shortbus that's only a novelty when it's not accidentally convenient.
I'd love to hear more about what you think the value proposition is. I'm normally 30 min away from that heliport so I'd love to be able to take the offering more seriously.