A subway has none of these disadvantages, with the advantage of serving ~1.5k people at once as opposed to ~15, and the ability to not conflict for surface space.
Why are rich people who can pay a premium to "get there fast and in privacy" forbidden to land on buildings?
BLADE runs a helicopter shuttle today but I don’t think they land on skyscrapers.
That heliport also wasn't profitable during the few years it operated in the 1960s.
NYC does have https://en.wikipedia.org/wiki/Downtown_Manhattan_Heliport ("top business executives and time-sensitive document deliveries often use the heliport", as well as tourists and others) but it's on a pier, not on a roof.
The toy "indoor" helicopters demonstrate this easily; they don't like to get near "things", or they like it too much.
even in rural areas "air ambulances" run from designated pickup points and win on being able to do straight line flights (debatable, there's arguments to be made they're not a "win" at all). they can't land just anywhere; and there's a surprising volume of space and maintenance need for a viable landing spot.