You mentioned that your protagonist would be flying to a private heliport. However, if the helicopter flies to DCA (Reagan National), they would have to depart from one of about 18 "Gateway" airports, AND carry a TSA-approved
armed security guard (ASO, or private air marshall) in addition to the numerous paperwork hoops to jump through to land there. They wouldn't be able to make this flight direct from any of the 3 NYC heliports as none are approved as a gateway airport (despite standard TSA screening), but would most likely make a pitstop at Teterboro for that screening. Read more about the DCA Access Standard Security Program (DCASSP)
here.
This is only for GA aircraft and only applies to DCA Airport, not a private heliport.